PROCEDURE FOR THE PRODUCTION OF NEW AMINOBENZYLAMINEN AS WELL AS THEIR SOUR ADDITION SALTS

The subject of the invention is a procedure for the production of new benzyle amines of the general formula - n, IL \ R-S (1) and of them physiologically compatible salts with inorganic or organic acids. In the above general formula (I) mean g 1 hydrogen or an aliphatic or an aromatic acyl group, R2 hydrogen, chlorine or bromine, R3 FIuor, a geradkettige or branched alkyl group with i to 4 carbon atoms, which TrifluormethyI, cyanogen, Carbamoyl, carboxyl, Carbalkoxy, Alkoxy, AcetyI, 1-Hydroxyäthylgruppe or a Arn nomethylgrnppe of the formula whereby R6 and R7 independently alkyl, Cycloalkyloder Hydroxycycloalkylgruppen or together with the Stickstoffatozn a Pyrrolidin, Piperidinoder Morpholinring represent, R4 and R5 replaced independently hydrogen, geradkettige or branched alkyl groups with 1 to 5 carbon atoms, which with 1 or 2 hydroxy groups can be replaced, groups of alkenyls with 2 to 4 carbon atoms, if necessary with or two hydroxy groups CycIoalkylgruppen with 5 to 7 carbon flavours, benzyle, Morpholinooarbonylmethylgruppen or together with that nitrogen bases a Pyrrolidin, a piperidin, a hexadecimal hexadecimalaminehexadecimal amine, a Morpholin, N-methyl-piperazin-or Camphidinring. The connections of the above general formula (I) exhibit valuable pharmakologische Eigensohaften, in particular an anti- Uleus effect, a sekretolytische, cough-satisfying and an increasing effect on the production of the Surfactant or Antiatelektase factor of the alveoles. The new connections let manufacture itself-following procedure: Conversion of a benzyle connection of the general formula B J. CH2 R2 N (g 1 - x in the blanks and R2 like initially are defined, R the remainder - CH2 - X or the meanings mentioned initially for RA possesses and X chlorine, bromine or iodine, which means hydroxy group, a Acyloxy, Sulfonyloxy, Alkoxy, A of ryloxyoder Aralkoxygruppe, a group of tri alkyl ammonium or the Pyridiniumgruppe, with an amine of the general formula (in) in the R4 and R5 like initially is defined. In the above general formula (IL) in particular the meaning chlorine or bromine for X, which hydraulic XY, Acetyloxy, Butyryloxy, Benzoyloxy, NIethylsulfonyloxy, p-Toluolsulfonyloxy, Methoxy, Äthoxy, Phenoxy, Trimethylaroniumoder l&gt, comes; yridinin.mgruppe in consideration; X can mean thus each withdrawing group, those intermediately the formation of a benzyle cation, on the basis of a connection of the above general formula (II), made possible. The conversion takes place appropriately in suitable Lösungsmittelwie Tetraehlorkohlenstoff, chloroform, methanol, tetrahydrofurane, benzene, toluol, ether, Dioxan, Tetrain or in a surplus of the used amine of the general formula (REAR ONE) and depending upon the Reaktioasfählgkeit of the remainder of X at temperatures zwis -70 and 200co chen. The Urnsetzung can be accomplished however also without solvents. If the conversion with a connection of the general Forn becomes el (II) accomplished, in the X the hydroxyl group represents and is in 2-Stellung an ecyl amino group, then the acyl group can during the conversion abgespalten to become. If X means a Sulfonyloxygruppe as for example the 4-Methylphenyl-sulfonyloxygruppe, then the conversion is preferably accomplished at temperatures between -70 and 50°C into a kind of solution ttelwie for example an aliphatic or cyclischen ether. If X halogen means, then the conversion becomes preferably at temperatures between 0 and 150°C, e.g. with the boiling temperature of of the used solvent, and appropriately in presence of of a hydrogen halide-binding means, e.g. an inorganic base such as Natriumcarbonat or Natrlumhydroxyd, an ion exchanger, a tertiary organic base such as tri ethyl amine, Pyridin or in a surplus of of the used amine of of the general formula ([IL) accomplished. Hiebei can serve a used tertiary organic base also at the same time as solvents. If X means a Acyloxygruppe as for example the Acetoxyoder Benzoyloxygruppe or a Alkoxy, Aryloxyoder Aralkoxygruppe, then the conversion is preferably accomplished if necessary in present one to drink catalyst such as ammonium chloride, sourer alumina or sulfuric acid, and at temperatures between 0 and 200°C. If X means the hydroxyl group, then the Urnsetzung is accomplished if necessary in present one to drink catalyst such as sulfuric acid, hydrobromic acid, p-Toluolsulfonsäure, a low carbonic acid such as Propionsäure or Butters äure or if necessary in presence of an alkaline catalyst such as potassium hydroxide, magnesium oxide or Natriumarnld, preferably at temperatures between 120 and 180°C. The conversion can be durchgefiihrt however also without solvents. If X means a Trialkylammoniumoder Pyrtdiniumgruppe, then the Urnsetzung preferably becomes in a surplus of the used amine of the general formula (ii) accomplished as solvents at temperatures between 120 and 180°C. The conversion can be accomplished however also without solvents. If one receives a connection of the general formula (I), in which R3 represents the Cyaugruppe, then this can by means of partial hydrolysis, e.g. by means of w of serig alcoholic caustic soda solution, into which appropriate Carbarnoylverbindung of the general formula (I) to be transferred, and/or a connection of the general formula (I), in that g 1 hydrogen represents and R-S, 1 4 and I 5 with exception of hydrogen and the one reactive hydrogen atom containing remainder like initially is defined, then this can later be acyliert gewünschtenfalls. This conversion appropriately accomplished with one reat ionsf h_tgen acid derivative like a Säurehalogenid, a Säureanhydrid or a mixed Säureauhydrid or in presence of an water-withdrawing means such as N, N' - Dicyclohexyl carbodifmld. The received connections of the general formula (I) can gewünschtenfalls with be anorgauisehen or organic acids into their physiologically compatible acid addition salts also, two or three Äquivaleuten of the acid concerned be transferred. As acids for example hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, Milehsäure, citric acid, Wefnsäure, maleic acid or fumaric acid as suitably proved. The connections of the general formula (II) used as basic materials can be manufactured in usual procedures, e.g. by conversion of the appropriate toluol derivatives with N-Bromsuccinimid and/or with halogen under UV irradiation, from the appropriate benzyle alcohols with Thionylchlorld or through around etzung an appropriate benzyle halide with an alkali salt of a carbonic acid, with an alkene all alcoholate or - phenolat or by Halogenferung of an appropriate benzyle ammonium salt, by conversion of an appropriate benzyle halide with an appropriate amine, by l eduktion an appropriate aldehyde or by Verseffung of an appropriate benzyle halide. As mentions already initially, possess the new connections of the general formula (I) valuable pharmakologische characteristics, in particular an anti- Ulcus effect, a sekretolytische, cough-satisfying and an increasing effect on the production of the Surfactant or Antiatelektase Fakters of a1veolen. For example the following substances were examined for their biological effects: A = 2-Amino-3-bro n-5-carbäthoxy-N, N-diäthyl-benzylamin-hydrochlorld, B = N-Äthyl-2-amino-3-brom-5-carboxy-N-cyclohexyl-benzylamin-hydrochlorid, C = N-Äthyl-2-amino-5-brom-N-cyolohexyl-3-fluor-benzylamin-hydrochlorid, D = n (2. mino-5-brom-3-methyl-benzyl} - hexarnethylenamin dihydroeMorid, E = n (2-Amino-5-brem-4-tert. butyl benzyle) - morpholin dihydrochlorid, F = 5-Acetyl-2-amino-3-brom-N, N-dimethyl-benzylamin and G = 2-Amino-3-brom-N, N-dimethyl-5-fluor-benzylamin-hydrochlo identification. - - I R. 33z375 ith Sekretolyti effect: The Expekterationsversuche became at anaesthetized guinea pigs or at anaesthetized rabbit (S. hiezu Terry and Boyd, Pharnmcol. exp. Therap. 73, P. 65) accomplished. The substances became in each case 6 to 8 depths in a dose of 8 mg/kg p. o. appliziert. The computation of the secretion increase (2-Stunden-Werte) took place via comparison the secretion quantity after and before substance gift: The cycle attempts were accomplished in each case 3 cats in Chloralose Urethau anaesthesia after intravenous gift by in each case 2, 4 and 8 mg/kg the substance which can be examined: Attempts at guinea pigs: Substance secretion increase A B C G + 90% + 81% +100% + 84% cycle effect 2, 4 and 8 mg/kg: no change 2, 4 and 8 mg/kg: no change of attempts outer rabbits: Substance secretion increase D +72% E +77 F +75% 2nd anti- Ulcus effect: The effect of the substance which can be examined on Ulcera became according to the method of K. Takagi et al. (Jap. J. Pharmac. i9, P. 418) determines. Hiezu was opened female rats with a body weight between 220 to 250 g in ether arcose the Banchhöhle and the stomach was out-stored. Afterwards between Muscularis mucosae and the Submukosa of the stomach in a place 0, 05 mI were injected a freon ssigsäurelösung. The abdominal cavity was again closed after the injection. After 3 to 5 days at the application place in the mucous membrane developing the ulcers were treated 3 weeks long by adding the substance in the dosages of 50 and 100, which can be examined, mg/kg to the fodder (6 animals/dose). The control animals received only the pulverized fodder. After three-week treatment those of animal were killed, which stomach determines taken and the Ulcera by measurement of the Geschwürläuge and ulcer width. s was determined in relation to substance effect Kent to roll (100%): With a dosing August the substance A of 50 mg/kg p.o became a reduction of the Uleeru around 52% and with a dosage of 100 mg/kg p.o a reduction of the Ulcera around 79 in relation to controls gefun - that. 3. Acute toxicity: The acute toxicity of the substances which can be examined determined at groups ven ever 5 white mice according to single-channel gift from 1000 and/or 2000 mg/kg p.o orienting: Substance acute Toxizit ät A B C D E F G > 2000 mg/kg p.o. (0 of 5 depths gestorbäu) > 1000 mg/kg p.o. (0 of 5 animals died) > 1000 mg/kg p.o. (0 of 5 animals died) > 1000 mg/kg p.o. (0 of 5 animals died) > 1000 mg/kg p.o. (0 of 5 animals died) 1000 mg/kg p.o. (2 of 5 depths died) > 1000 mg/kg p.o. (0 of 5 animals died) the new connections of the general formula (1) can be trained for pharmaceutical application into the usual phamazeutisehen preparation forms such as tablets, Dragdes, caps, Suppositerien, ampuls and solutions, if necessary in combination with other active substances. The single dose amounts to hiebei 1 to 100 mg, preferably 4 to 60 mg, and the daily dose 2 to 300 mg, preferably 4 to 200 mg. With connections with sekretolytischer effectiveness amounts to the Finzeldosis 1 to 20 mg, preferably however 4 to 15 mg, and with an Antiulcus effect 25 bie 100 mg, preferably however 30 to mg. The naohfolgenden Beisptele is to describe the invention more near: B e f s p i e I 1: 2-Amino-3-brom-N, N-dimethyl-5-fluor-benzylamin: 5, 5 g 2-Amino-3-brom-5-fluor-benzylaIkohol are solved in 150 ml chloroform. Under agitating and cooling with ice one admits drop by drop Thlonylahlorid to 7.13 g (4, 35 valley), whereby a yellow precipitation fails. One leaves the suspension untouched at ambient temperature over night and restricts then in the vacuum with RauIntemperatur at the rotation evaporator to the Trookne. In such a way won raw benzyle chloride is suspended in 100 ml chloroform. Under agitating one undK'ühien hiezu 20 ml Dimethylamin with is gives, how! 0 a clear solution one receives. One leaves 30 untouched min under ice cooling and extracts then twice with satisfied Kaltumcarbonat solution. The chloroform phase is washed with water, getrockuet over sodium sulfate and evaporated in the vacuum to the Troelme. The arrears are taken up in absolute Ättmnol and addressed with ethereal hydrochloric acid to pH 3. The failed hydrochloride is sucked off and solved in absolute Ä nol. After additive of activated charcoal the solution is heated up for simmering. After Abftltrieren of the activated charcoal and after additive of ether one receives colorless crystals. Sehmelzpunkt: 9.41 to 243°C. B e i s p i e I 2: 2-Acetylamino-N, N-dläthyl-3-methyl-benzylamin: 22 g 2-Aeetylamino-3-me yl-benzylbromtd are shifted in 1, 6 I carbon tetrachloride with 20 g Diäthylamin and 1 h at the return flow is cooked. Subsequently, the reaction solution is restricted, which arrears in 1 1 2n hydrochloric acid solved, twice with chloroform out-vibrated, which extracts sour phase with concentrated ammonia alkaliseh posed and three times with chloroform. The organic phase is restricted and the arrears over silicagel with acetone methanol (9 • 1) chromatographiert. The received raw product Iöst one in ethanol, acidifies with äthanolischer tartaric acid and brings by additive of ether the 2-Acetylamfno-N, N-diätbyI-3-methyl-benzylamin as Tartrat to the crystallization. Fusion point: 134 to 136°C. B e i s p i e I 3: 2-Acetylarntno-5-brom-N, N-diäthyl-3-diäthylaminomethyl-benzylamin: 16, 5 g 2-Acetylamino-5-brom-3-brommethyl-benzylbremtd are shifted in 1, 6 1 carbon tetrachloride with 24 g Diäthylamin and cooked I h at the return flow. The reaction solution is solved afterwards restricted, the Rüokstand in 0,7 1 2n hydrochloric acid, out-vibrated twice with chloroform, which extracts salt-sour phase with concentrated ammonia alkalinely posed and three times with chloroform. One dries and distills the organic phase with sodium sulfate the solvent off. One separates the arrears sRulenchromatographisch over silicagel with ethyl acetate methanol (1: 1), restricts it combines the appropriate parliamentary groups to dry ones and receives by Umkristalltsatton from Petrologe the 2cetylamino-5-brom - N, N-diäthyl-3-diäthylaminomethyl - benzyle amine. Fusion point. 91,5 to 93°C. B egg FR i el 4: 2-Aeetylamino-5-brom-4-tert. butyl n cyclohexyL N METHYI benzylaming 2-AceWlamino-5-brom-4-tert. butyl benzylbromid in 1, 5 1 carbon tetrachloride with 23 g is cooked, cooled down N-methyl-cyclohexylamin for 1 h at the Rüekfluß, filtered off the failed N-Methylcyclohexylamin-hydrobromid and restricted the filtrate. The 1Rückstand one shifts with 2n hydrochloric acid and extracts twice with benzene. The sour phase is alkalinely placed with concentrated ammonia, out-vibrated three times with chloroform, dried and restricted the organic phase. The arrears become säulenchromatographisch over silicagel with ethyl acetate chloroform (1: !) cleaned and from Äthauol ether with äthanolischer hydrochloric acid the 2-Acetylamino-5-brom-4-tert. butyI n eyclohexyL N METHYLBENZYLAMIn hydroehlorid pleases. The Rchprodukt is recrystallized from ethanol ether. Fusion point: 231 to 234°C. B e i s p i e I 5: Z-Acetylamino-4-tert. butyl-5-chlor-N-cyclohexyl-N-methyl-benzylamin: 29 g 2-Acetylamino-4-tert. butyl-5-chlor-benzylbromfd are cooked, cooled down for 2 h at the return flow into le 5 1 carbon tetrachloride with 26 g N-methyl-cyclohexylamin, filtered off N-methyl-cyclohexylamin-hydrobromid and restricted the filtrate. The arrears are out-vibrated to concentrated ammonia taken up to 2n Esefgsäure, with chloroform, the sour phase wit alkalinely placed, three times with chloroform extracted and hare restricted the organic I. After säulenchromatographlscher Beinigung over silicagel with ethyl acetate chloroform (1: 1) crystallizes the 2-Acetylamino-4-tert. le yI-5-chlor-N-cyclchexyl-N - methyl benzyle vn n from absolute ethanol and one do-crystallizes from Äthauol. Fusion point: 174 to 175, 5°C. Example 6:2 - Acetylamino-5-tert. butyl n cyclohexyL N METHYl benzylamin: 23 g 2-Acetylamino-5-tert. butyl benzylbromid in 1, 6 is cooked 1 carbon tetrachloride with 24 g N-methyl-cyclohexylamin I h at the return flow. After the cooling one filters off N-methyl-cyclohexylamin-hydrobromid, restricts the filtrate and cleans the raw product säulenchromatographisch over silicagel with ethyl acetate. The appropriate parliamentary groups are restricted and the 2-Ace ylamino-5-tert. butylùN-cyclohexyl-N-methyl-benzylamin from petroleum ether crystallizes. Fusion point: 111 to 112” 5°C. B e i s p i e 1 7: 4-Aee ylamino-3-text. butyl n cyclohexyL N METHYl benzylamin: 56 g 4-Acetylamino-3-tert. butyl benzylbromid in 500 ml IethyI cyclohexyI n 1, 5 h are cooked for chloroform with 48 g N-I afterwards at the return flow, to-vibrated three times with water and restricted the organic phase. The arrears become oäulenchromatcgrapbisch over silicagel with chloroform ME hauol (5: 1) cleaned and the 4-Ace yI ino-3-tert. butyl n cyclohexyL N METHYl benzyla n-hydrechlorid from absolute ethanol ether under additive of absolute äthanolischer hydrochloric acid crystallizes. Fusion point: 240 to 243°C (Zers.). Example 8:5 - Acetyl-2-Acetylen-N, N-dimethyl-benzyle n: 21 g 5-Acetyl-2-acety ino benzylbremid are shifted in 500 ml chloroform with 8,1 g Dimethylamin and agitated 30 min. With using exothermic l eakt; ion dissolves the substance. Subsequently, the Reak is out-vibrated ienslösung three times with water and twice with 2n hydrochloric acid. The salzsanre phase is extracted with chloroform, placed with 2n ammonia alkalinely and out-vibrated twice with chloroform. The organic phase is restricted, the 1Rückstand s iulenchromatographisch over silicagel with ethyl acetate is cleaned and the appropriate parliamentary groups is combined and to dry ones restricted, whereby one keeps 5-Acetyl-2-acetylamino-N crystalline, N-dimethyl-benzylamin. Sehmelzpunkt: 68 to 72ec. B e i s p i e I 9: 2-Anno-3-brom-5-carbamoyl-N, N-diäthyl-benzylamin: 11 g 2-Amino-3-brem-5-cyan-N, N-diäthyl-benzylamin is cooked with 70 mi Äthauol and 100 nl 5n caustic soda solution at the return flow. After the cooling with 100 ml water is diluted and extrabiert with chloroform. The chloroform excerpt is getroeknet, restricted over sodium sulfate and recrystallized the l ückstaud made of isopropanol. One receives 2-Amino-3-brom-5-carbamoyl-N, N-diäthyl-benzyle u n from the point of fusion 140 to 142°C. Example 10:2 - Acetamino-5-carbäthoxy-N, N-diäthyi-benzylarùin: g 2-Acetamid-5-carbäthoxy-benzylbromid are solved in 400 ml chloroform and 100 ml ethanol and cooked with 22 g Di £hylamin 1 h under return flow. One cools down, restricts in the vacuum, distributes the arrears between diluted ammonia and chloroform, the dry chloroform solution over Natrinmsulfat and restricts her in the vacuum. DerlRückstand is cleaned by chromatography at silicagel (Elutiensmitteh ethyl acetate). The received 2-Acetum-5-earbäthoxy-N, N-diäthyI-benzyIarùin is umk_ristaUlsiert from ethanol. Fusion point: 57 to 59°C. B e i s p i e i 1 1: 2-Amino-Ne-cyclohexyl-N-methyl-3-trffinormethyl-benzylami: g 2-Ascot-3-trifluormethyl-benzylalkohol are solved in 200 ml chloroform and shifted in the process from 10 n n under agitating drop by drop with 15,9 mi Tbionylchlorid. Subsequently, one cooks still 90 min under return flow. One cools down and removes in the vacuum carefully all Fluchtige. The received arrears at raw benzyle chloride one loosens chloroform in 200 ml. Under mechanical agitating and ice cooling one adds 38.1 g within 10 min N-methyl-cyciohexylamin and leaves afterwards 18 h untouched with for instance 20Oc. One washes ges with ätt igter potassium carbonate solution, trockuet and removes the solvent in the vacuum. The oily Eindampfrückstand is cleaned by Chromatograpbie over a Eieselgelsäule (Laufmittel: Chloroform: Methanol = 9: 1). The received, again oily Eindampfrückstand becomes in a mixture from ether and Easigester (1: 1) solved. The 2-Amino-N-c yclohexyl-N-methyi-3-trifluormethyl-benzylamln-hydrochlorid is crystalline separated by addition of isopropanolischer hydrochloric acid. After twice recrystallizing from IsopropauoI the fusion point amounts to 203 to 206°C. Example i2: 2-Amino-5-carbameyl-N, N-diäthyl-benzylamin: g 2-Abgetane-5-cyau-N, N-diäthyl-benzyla in become 4 h long with 100 rel. 511 Natrenlauge and 70 ml ethanol cooked. One cools, diluted with 200 ml water down and extracts three times with ever 250 ml chloroform. The Chleroformiösung is dried over sodium sulfate and restricted in the vacuum. The arrears are recrystallized from ethanol. Mau receives 2-Amino-5-carbamoyl-N, N-diäthyl-benzyle r-in of the fusion point 129 to 131°C. B e i s p i e i 1 3: 2-Aeeta n uo-N-tert. butyi - carbäthexy benzy u fusion point: 136 bis139°C. Made of 2-Aceh nino-5-carbäthoxy-benzylbromid and save. Le ylamin similar to example B e i s p i e i 14: 2-Acetarù uo-5-carb thoxy n cyclohexyL N METHYl benzylamin: Fusion point: 71 bis74°C0 made of 2-Acet rù o-5-carbäthoxy-benzylbremid and N-methyl-cyclohexylamin similar to example with FR IE i 1 5: 2-Acetar ino-N-äthyl-5-carbäthoxy-N-cyclohexyl-benzylamin: Fusion point: 92 to 95°C. Made of 2-Acetat-5-carbäthoxy-benzylbromid undN Äthylcyclohexylamin similar example B e i s p i e 1 1 6: N (2-Aoets uo-5-carbäthoxy-benzyl) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point: 100 to 102°C. Made of 2-Acetamino-5-carbä hoxy benzylbromid and hexadecimal hexadecimalaminehexadecimal amine similar to example B e i s p i e 1 1 7: 2-Amino-Ne-tert. buW1-5-carbamoyI-bcmzylamin: Fusion point of the hydrochloride: 120 to 130°C. Manufactured by soaping of 2-Aceßmino-N-tert. butyl-5-cyanbenzylamin in caustic soda solution similar to example 12. B e i s p i e 1 1 8: 2-Amino-3-brom-N-tert. butyI-5-earbamoyl-benzylamtn: Fusion point of the hydrochloride: 160 to 170°C. Manufactured by soaping of 2-Amino-3-brom-N-tert. butyl-5-cyan-benzylamin in caustic soda solution similar to example 9. B e i s p i e I 1 9: 2-Amino-5-carbamoyl-N-cyclohexyl-N-methyl-benzylamin: Sehmelzpunkt: 142 bis143°C. Manufactured by Verssifung of 2-Amino-5-cyan-N-cyclohexyl-N-methyl-benzylamin in caustic soda solution similar to example 9. B e i s p i e I 2 0: 2-Amino-3-brom-5-carbamoy! - N-cyclohexyl-N-MSTHYL-benzylamin: Sehmelzpunkt: 150 to 152°C. Manufactured by Verseißmg of 2-Amino-3-brom-5-cyan-N-cyclohexyl-N-methyl-benzylamin in caustic soda solution similar to Beispie! 9. B e i s p i e 1 2 1: NT yl-2-amine-5-carbamoyI-N-cyciohexyI-benzylamin: Fusion point: 136 to 138°C. Manufactured through soaping of N-Athyl-2-acetamino-5-cyan-N-cyclohexyI-benzylamin in Natrenlauge similar to example 12. B e i s p i e 1 2 2: N-Äthy [- 2-amino-3-brom-5-carbarnoyl-N-cyclohexyl-benzylamin: Fusion point: 144 to 146°C. Manufactured through soaping of E-Äthyl-2-amino-3-bro n-5-cyau-N-cyclohexyl-benzylamin inNatr (mlauge similar to example 9. B e i s p i e 1 2 3: N (2-Amino-5-carbamoyl-benzyl) - hexamethyienamin: Fusion point: 115 to 1180C. Manufactured by soaping of n (2-Amino-5-cyan-benzyl) - hexadecimal hexadecimalaminehexadecimal amine in caustic soda solution similar to example 9. B e i s p i e 1 2 4: N (2-Amino-3-brom-5-carbamoyl-benzyl) - hexamethylm amine: Sehmelzpunkt: 155 to 157°C. Manufactured by Verseffung of n (2-Amino-3-brom-5-cyan-benzyl) - hexadecimal hexadecimalaminehexadecimal amine in caustic soda solution similar to example 9. B e i s p i e 1 2 5: 2-Acetamino-5-cyau-N, N-dimethyl-benzyle me: Fusion point of the hydrochloride: 244 to 245°C (Zers.). Made of 2-Acetamino-5-cyau-benzyibromid and Dimethylamin similar to BeispieI B e i s p i e 1 2 6: 2-Acetamino-5-cyan-N, N-diäthyl-henzylarnin: Sehmelzpunkt: 80 to 82°C. Made of 2-Acetamino-5-cyan-benzyIbromid and Diäthylamin similar to example B e i s p i e 1 2 7: 2-Aeetamino-5-cyau-N, N-dipropyl-benzylamin: Fusion point: 80 to 82°C. Made of 2-Acetamino-5-cyan-benzyIbromid and Dtpropylamin similar to example example 28:2 - Aestamino N tert. buWI-5-cyan-benzylamin: Fusion point of the hydrochloride: 260 to 265ec. Made of 2-Acetamine-5-cyan-benzylbromid and tert. BuWlamin similar to example B e i s p i e 1 2 9: 2-Acetamtno-5-cyan-N-cyclohexyI-N-methyl-benzylamin: Fusion point: 116 to 118°C. Made of 2-Acetamtno-5-cyan-benzylbromid and N-MethyI-cyclohexylamin similar to example B e i s p i e 1 3 0: 2-Acetamin0-N-äthyl-5-cyau-N-cycl0hexyl-benzylamin: Fusion point: 85 to 88ec. Made of 2-Acetamino-5-cyau-benzylbromid and N-i thyl cyclohexylamin similar to example B e i s p i e 1 31: 2-Acetamino-N-äthy! - N-benzyl-5-cyau-benzylamin: $ch_melzpunkt: 112 to 113°C. Made of 2-Acetamino-5-cyan-benzylbromid and N-ethyl-benzylamin similar to example B e i s p i e 1 3 2: 2-Acetamino-N-benzyl-5-cyan-N-propyl-benzylamin: Sclunelzpunkt: 109 to 111°C. Made of 2-Acetamino-5-cyan-benzylbromid and N-Propyl-benzylamin similar to example B e i s p i e 1 3 3: 2-AceHTù no-N-benzyl-N-butyl-5-cyan-benzylarù n " fusion point: 65 to 66°C. Made of 2-Acetamid-5-cyan-benzylbromid and N-Buty! - benzyle amine similar to example B e i s p i e 1 3 4: N (2-Aeeta no-5-cyan-benzyl) - hex ethylenar in: Sehmelzpunkt: 108 to 110°C. Made of 2-Aeemn ino-5-cyan-benzyl-bromid and He methylena n similar to example with spie i 3 5: 2-Amino-3-brom-N, N, 5-trimethyl-benz'y ù n. Sehmelzpunkt of the Hydroehlorids: 216 to 217oc. Made of 2-Amino-3-brom-5-methyl-benzylalkohol, Thionylchlorid and Dimethyla n similar to example 1. B e i s p i e i 3 6: 2-Amino-N-ä hyl-3-brom-N, 5-de-ethyl-benzylamin: Sohmelzpunkt of the Hydroehlorids: 199 to 200°C. Made of 2-Anno-3-brom-5-methy! - benzyle alcohol, Thionylchlorid and N-Methy! - ethyl amine similar to example 1. 1 example 37:2 - Acetamino n, N-diäthy! - 5-methyi-benzylamin: Sehmelzpunkt of the Hydroehlorids: 184 to 186°C. Made of 2-Aoetamino-5-methyl-benzyl-bromid and Diäthylamin similar to example 6. B e i s p i e i 3 8: 2-Anno-3-brom-N, N-diäthyl-5-methyl-benzylamin: Sehmeizpunkt of the Hydroehlorids: 205 to 207°C. Made of 2-Anno-3-brom-5-methyl-benzylalkohol, Thionylchlorid and Diä hylamin similar to example i. B e i s p i e I 3 9: 2-Acetamid-N-cyelohexyl-N, 5-diInethyl-benzylarain: SehInelzpunk% of the Hydroehlorids: 9,22 to 223°C. Made of 2-Aeets ino-5-methyl-benzylbromid and N-methyl-cyelohexylaxnln similar to example 6. 9.5 example 40:2 - Ainino-3-broIn-N-oyolohexyl-N, 5-dilne hyl benzylamin: Sehmelzpunkt of the hydrochloride: 223 to 224°C. Made of 9-Amino-3-brom-5-methyl-benzylalkohol, Thionylehlol4d and N-methyl-cyelohexylamin similar to example 1. B e i s p i e 1 1: 2-Alnino-3-brom-N, 5-dime hyl n (cis-3-hydroxy-cyelohexyl) - benzyle in: Fusion phase of the Hydroeblorids: 198°C. Made of 2-Amlno-3-brom-S-methyl-benzylalkoho! , Thionylchlorid and N-Methyl-cis-3-hydroxy - cyc! ohexylamin similar to example 1. With spie i 42: 2-Aeetamino-N-äthyl-N-cyclohexyl-5-methyl-benzy m n: Sehmelzpunkt of the Hydroehlor [DS: 224 to 225°C. Made of 2-Aeetamino-5-methyl-benzylbromid and N-Ätäyl-cyelohexylamin similar to example 6. B e i s p i e 1 4 3: 2-Amino-N-äthy! - 3-brom-N-cyclohexyl-5-methyl-benzyl *n n: Sehmelzpunkt of the Hydroehlorids: 186°C. Made of 2-Binino-3-brom-5-methy! - benzyle alcohol, Thionyleh! orid and N-ethyl-cyelohexylamin similar to example 1. Example 44:2 - Amino-3-brom-N, 5-dimethyl-N (trans-4-hydroxycyclohexyI) - benzyle amine: Sehmelzpunkt of the Hydroehlorids: 212°C. Made of 2-Anno-3-brom-5-methy! - benzyle alcohol, Thionylehlorfd and N-Methyl-trans-4-hydroxy-oye! ohexylamianalog example 1. B e i s p i e 1 4 5: 2-Ainino-N-benzyl-3-brom-N, 5-dimethyl-benzylamin: Sehmelzpunkt of the Hydroehlorids: 220 to 222°C. Made of 2-Anno-3-brom-5-methyl-benzylalkohoI, Thionylchlorid and N-methyl-benzylamin similar to example 1. B eispie i 4 6: N (2-Amino-3-brom-5-methyl-benzyl) - pyrrolidin: Sehmelzpunkt of the Hydroehlorids: 179 to 181°C. Made of 2-Amino-3-brom-5-methy! - benzylalkDhol, Ttüonylehlorid and Pyrrolidin similar to example 1. B e i FR i e 1 4 7: N (2-Amino-3-brom-5-methyl-benzy!)- piperidin: Fusion point of the Hydroehlorids: 238 to 239°C. Hergestelt from 2-Ainino-3-brom-5-me hy! - benzyle alcohol, Thionylchlorid and Piperidin similar to example 1. B e i s p i e 1 4 8: N (2 - Ar-in-3-brom-5 - methyl beuzyl) - morpholin: Sehmelzpunkt of the Hydroehlorids: 243 to 244°C. Made of 2-Binino-3-brom-5-methyl-benzylalkohol, Thiony! ehlorid and Morpholin similar to example 1. B e i s p i e 1 4 9: N (2-Acetarnino-5-methyl-benzyl) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point of the hydrochloride: 164 to 165°C. Made of 2-Acetamino-5-methyl-benzylbromid and hexadecimal hexadecimalaminehexadecimal amine similar to example 6. With FR i e 1 5 0: N (2-Arnino-3-brom-5-methyI-benzyl) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point of the Hydrechlortds: 193 to 194°C. Made of 2-Amino-3-brom-5nethyl-benzylalkohol, Thionylchlorid and HexamethyIenamln similar to example 1. B e i s p IE 1 51: 2-Amino-N, N-dimethyl-5-methoxy-benzylamin: Made of 2-Amino-5-methoxy-benzylalkohol, Thionylchlorid and Dimethylamin similar to example 1. Structural proof by IR, UVund NMR spectra. ] R-spectrum (iVlethylenchlorid): 3280 cm-i NH2 3420 cm-i NH2 2780 cm-t N (CH 2 2830 cm-t OCH3 1600 cm-t C=C B e i s p i e I 5 2: 2-Amino-N, N-diäthyl-5-methoxy-benzylamin: Made of 2-Amino-5-methexy-benzylalkohol, Thienylchlorid and Diäthylamin similar to example 1. Structural proof by IR, UVund NMR spectra. IR-Spektrtun (dichloromethane) “3260 cm-1 NI-I2 3410 cm! NI-I2 2830 cm-t OCHs 2800 cm-i N-ethyl 1510cm-1 C=C 1600 cml 3280 cmt 3410 crn t 2830 cm-i 2800 cmt 1500 cmt 1600 cm” t C=C B e i s p i e 1 5 3: N (2-Amino-5-methoxy-benzyl) - morpholin: Made of 2-Amino-5-methoxy-benzylalkohol, Thionylchlorid and Morpholin similar to example 1. Structural proof by IRund UV spectra. IR spectrum dichloromethane): NH2 NH2 OCH3 N-alkyl C=C C=C B e i s p i e I 5 4: 2-Amino-Ne-cyelohexyi-5-methoxy-N-methyl-benzylamin: Made of 2-Amino-5-methoxy-benzylalkohol, Thionylchlorid and N-methyl-cyclohexylamtn similar to example 1. Strukturbewels by IRund UV spectra. IR spectrum (Methyienehlorid): 3240 NH2 3400 cmt cmt NH2 2780 cmt N-methyl 2830 cm-t OCH3 2850 cml aliphatic hydrocarbon 2930 cm-i aliphatic hydrocarbon 1500 cm-i C=C 1510 cm-1 C=C B e i s p i e 1 5 5: N-Äthyl-2-amino-N-cycIohexyl-5-methoxy-benzylamin: Made of 2-Amino-5-methoxy-benzylalkohoI, ThionyIchlorid and N-ethyl-cyclohe lamin similar to example 1. Structural proof by IRund UV spectra. IR spectrum (Methy [enchlorid): 3250 cm-t NH2 3400 NI-I2 2830 cm-i OCH3 2800 cm-1 N-ethyl (shoulder) cmt 2850 cm-t aliphatic hydrocarbon 2930 cm-1 aliphatiseher hydrocarbon 1500 cm C = C 1600em " u C =C B e i FR i e i 5 6: N (2-Amino-5-methoxy-benzyl) - piperidin: Made of 2-Amino-5-methoxy-benzylalkohol, Thionylehlorid and Piperidin similar to example 1. Structural proof by IRund UV spectra. IR spectrum (Methylenehlorid): 3260 cm-1 NI-I2 3410 cm-1 example 57:2 - Amino-3-brom-N, N-diäthyl-5-fluor-benzyl ù " fusion point ttydrochlorids: 182 to 184°C. Made of 2-Amino-3-brom-5-fluor-benzylalkohol, Tbionylchlorid and Diäthylamin similar to example i. B e i s p i e I 5 8: N-Äthyl-2-amino-3-brom-N-eyelohexyl-5-fluor-benzyJ A n. Sehmelzpunkt of the Hydroehlorids: 176 bis178°C. Made of 2-An-o-3-brom-5-fluor-benzylalkohol, Thionylchlorid and N-Äthyl-eyclohexylarùin similar to example 1. B e i s p i e 1 5 9: N-Äthy! - 2-arù o-3-hrom-5-fluor-benzylamin: Fusion point of the hydrochloride: 210 to 212°C. Made of 2-Arvon-3-brom-5-fluor-benzylalkohol, Thionylehlorid of and ethyls n n similar to example 1. B e i s p i el 6 0: 2-Amino-3-brom-N, N-dimethy! - 5-fluor-benzylamin: Fusion point of the hydrochloride. 241 to 243°C. Made of 2-Amino-3-brom-5-fluor-benzylalkoho [, Thionylehlorid and Dimethylamin similar to example I. Example 61:2 - Arù no-3-brom-N-eyclohexyl-5-fluor-benzylamin: Fusion point of the hydrochloride: 250 to 25Z°C (Zers.). Made of 2-Amino-3-brom-5-fluor-benzylalkoho! , Thionylchlorid and cyclohexyl amine similar to example 1. B e i s p i e 1 6 2: 2-Amino-3-brom-5-fluor-N-methyl-benzyIRmin: Sohmelzpunkt of the hydrochloride: 215 to 217°C (Zers.). Made of 2-Amino-3-brom-5-fluor-benzylaIkohol, Thionylchlorid and Methylam n similar to example 1. B e i s p i e i 6 3: 2 - Acetylamino - 5-brom-N-cyeIohexyl-N-methyl-3 (N-methyl-cyclohexyl-aminome - thyl) - benzyle amine: Fusion point: 194 to 199°C. Made of 2-Acetylernino-5-brom-3-brorùmethy! - benzyle bromide and N-Methy! - cyclohexyl amine similar to example 3. B e i s p i e! 6 4: 2-Acetylamino-5-brom-N (traus-4-hydroxy-cyclohexyI) - N-methyl-3 [N-methyl (trans -4-hydroxy-cyelohexyle r - o) - methyl] - benzyIamin: Schmeizpunkt: 208 to 209°C. Made of 2-AcetyLarùino-5-brom-3-broTùrùethyl-benzylb, romid and trans-4-Methylamino-cyclohexanol similar to example 3. B e i s p i e I 6 5: 2-Acetylamino-N, N, 3-trimethyl-benzylRrnin: Sehmelzpunkt of the Hydroehlorids: 102 to 164°C. Made of 2-AcetylRmino-3-methyl-benzylbromid and Dimethylavni similar to Beispie! 2. B e i s p i e i 6 6: 2-Acetylase-o-N-äthyl-N, 3-dimethyI-benzyl-m n: Fusion point of the hydrochloride: 168 to 170°C. Made of 2-Aeetylamino-3-methyl-benzylbromid and N-methyl-ä hyI r - similar to example 2. Example 6 7: 2-Acetyla ino n, N-dipropyl-3-methyl-benzylarùin " Sehmelzpunkt of the hydrochloride: 156 bis159°C. Made of 2-Acetylsrn o-3-methyl-benzylbromid and Dißropylamin similar to example 2. B e i s p i e [6 8: 2-Acetylamino-5-brom-N, N, 3-trimethy! - benzyle amine: Fusion point: 114 bls 116°C. Made of 2-Aeetyl, mlno-5-brom-3-methyl-benzylbromid and Dimethylamin similar to example 2. Example 69:2 - Acetylavù no-N-äthyl-5-brom-N, 3-d ethy! - benzyle amine: Point of pain: 81 to 83°C. Made of 2-Acetylamino-5-brom-3-methyl-benzylbromid and N-Methyläthylamin similar to example 2. B e i s p i e I 7 0: 2-Acetylamino-5-brom-N, N-diäthyl-3-methyl-benzylamin: Sehnlelzpunkt of the Hydroehlorids: 192, 5 to 194°C. Made of 2-Acetylaminoß - brom-3-methyl-benzylbromfd and Dläthylarnin similar to example 2. B e i s p i e 1 71: N (2-Aeetylarnino-5-brom-3-methyl-benzyl) - pyrrolidin: Sehmelzpunkt: 123 bis127°C. Made of 2-Aeetylamino-5-brom-3-methyl-benzylbromid and I> yrrolidin similar to example 2. B e i s p i e 1 7 2: N (2-Acetylazaino-5-brom-3-methyl-benzyl) - piperidin: Sehmelzpunkt: 119 to 124°C. Made of 2-Acetylamino-5-brom-3-methyl-benzylbromtd and Piperidln similar to example 2. Example 73: N (2-Acetylamino-5-brom-3-methyl-benzyl) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point: 129 to 132°C. Made of 2-Aee ylamino-5-brom-3-methyl-benzylbromld and hexadecimal hexadecimalaminehexadecimal amine similar to example 2. B e i s p i e 1 7 4: N (2-Acetylamino-5-brom-3-methyl-benzyl) - morpholin: Fusion point: 105 to 110°C. Made of 2-Aeetylamino-5-brom-3-methyl-benzylbromtd and Morpholin similar to example 2. B e i s p i e 1 7 5: 2-Aeetylamino-5-brom-N-cyelohexyl-N, 3-dfmethyl-benzylamin: Sehmelzpunkt: 102 to 104°C. Made of 2-Acetylamino-5-broza-3-methyl-benzylbromid and N-methyl-cyelohexylamtn similar to example 2. With s p i e 1 7 6: 2-Aeetylamfno-5-brona-N, 3-dimethyl-N (cis-3-hydroxy-cyclohexyl) - benzyle amine: Sehmelzpunkt: 144 to 146°C. Made of 2-Aeetylamino-5-brom-3-rnethyl-benzylbromid and cis-8-Methylamlno-cyclohexanol similar to example 2. B e i s p i e 1 7 7: 2-Acetylamino-5-brom-N, 3-dimethyl-N (trans-4-hydroxy-cyclohexyl) - benzylamln: Schrnelzpunkt: 136, 5 to 138°C. Made of 2-Acetylamino-5-brom-3-methyl-benzylbromid and trans-4-Methylamino-eyclohexanol similar to example 2. B e i s p i e 1 7 8: 2-Acetylamino-N-äthyl-5-brom-N-cyclohexyl-3-methyl-benzylamin: Fusion point: 115 to 119°C. Made of 2-Aeetylamino-5-brom-3-methyl-benzylbromtd undN ethyl cyclohexylamin similar example 2. B e i s p i e 1 7 9: 2 Acety amine - N-äthy 5-br well n (trans-4-hydr XY cyc hexy) - 3 methy benzy amine: Fusion point: 168 to 170°C. Made of 2-Acetylamino-5-brom-3-methyl-benzylbrolnid and Bröns-4thylamino-cyclohexanol similar to example 2. B e i s p i e 1 8 0: 2-Aeetylamino-N-benzyl-5-brom-N, 3-dirnethyl-benzylamin: Fusion point: 97 to 99°C. Made of 2-Acetylsmino-5-brom-3-methyI-benzylbromtd and N-methyl-benzylamin similar to example 2. B e i s p i e 1 81: N (2-Acetylamino-5-brom-3-methyl-benzyl) - N' - methyl piperazLn: Fusion point of the Dihydroehlorids: 256 to 257°C (Zers.). Made of 2-Acetylamino-5-brom-3-methyl-benzylbromid and N-methyl-plperazin similar to example 2. Example 82:2 - Acetylamino-4-tert. butyl n cyclohexyL N METHYl benzyle vùtu. Schmelzpunk of the hydrochloride: 231 to 234°C. Made of 2-Aeetylamino-4-tert. butyl benzylbromid and N-methyl-cyelohexylamin similar to example 4. B e i s p i e 1 8 3: 2-Aeetylamino-5-brom-Lt-tert. Butyl n, N--dlmethyl benzylamin: Fusion point: ill to 113°C. Manufactured A s 2-Aeetylamino-5-brom-4-tert. butyl benzylbromid and Dlmethylamin similar to example 4. B e i s p i e I 8 4: 2-Acetylamino-5-brom--4-tert. Butyl n, N-di thyl benzylamin: Fusion point: 88 to 91°C. Made of 2-Acetylaml-o-5-brom-4-tert. butyl benzylbromid and Diäthylamin similar to Beisp lel 4. Example 85:2 - Acetylamino-5-brom-4-tert. Butyl n (hydroxy tert, butyl) - benzyle amine: Fusion point: 125 to 127°C. Made of 2-Aeetylamino-5-brom-4-tert. butyl benzylbromid and Hydroxy tert. butylamin similar to example 4. B e i s p i e I 8 6: N (2-Acetylamino-5-brom-4-tert. butyl benzyle) - pyrrolldin: Fusion point: 103 to 1070C. Made of 2-Aeetylarnino-5-brom-4-terk butyl benzylbromid and Pyrrolidin similar to example 4. With FR i el 8 7: N (2-Acetylamino-5-brom-4-tert. butyl benzyle) - piperidin: Fusion point: 132 to 1340C. Made of 2-Acetyl iuo-5-brom-4-tert. butyl ben - ylbromid and Piperidin similar to example 4. B e i FR i el 8 8: N (2-Acetylamino-5-brom-4-ter butyl ben yl) - morpholin: Fusion point: 136 to 139°C. Made of 2-Aeetylamino-5-brom-4-tert. butyl benzylbromid and Morpholin similar to example 4. Example 89:2 - Acetylamino-5-brom-4-tert. Butyl n (eis-3-hydroxy-cyclohexyl) - N-methyl-benzyle m'in: SchInelzpunkt. 167 to 1720C. Made of 2-Aeetylamino-5-brom-4-tert. butyl-benzylbromi4 and cis-3-Methylamino-cyclohexanol similar to example 4. With s p i e 1 9 0: 2-Acetylen-5-brom-4-tert. BuL yl n (trans-4-hydroxy-cyclohexyi) - N-methyl-b - Scb.melzpunkt. 174 bis17600. Made of 2-Acetylamino-5-brom-4-ter ylbromid and trans-4-methylamino-cyclohexanol butyl ben similar to example 4. Example 91:2 - Acetyla ino N ä hyl-5-bro -4-terk butyl N EYCLOHEXYL benzyle rni: Sckmeizpunkt: 102 to 105°C. Made of 2-Acetylase-5-brom-4-tert. butyl benzylbromid and lq-ethyl-eyclohexylamin similar to example 4. B e i s p i e 1 9 2: N (2-Acetylamino-5-brom-4-tert. butyl benzyle) - Nv - methyl piperazin: Fusion point of the Dihydrochlorids: starting from 2500C (Zers.). Made of 2-Acetylamino-5-brom-4-tert. butyl benzylbromid and N-Meübylpiperazin similar to example 4. B e i s p i e 1 9 3: N (2-Aeetylzmino-5-brom-4-tert. butyl benzyle) - camphidin: Fusion point: 133 to 138°C. Made of 2-Acetylarnlno-5-brorn-4-tert. butyl benzylbromid and Camphidin similar to example 4. B e i s p i e 1 9 4: 5-Acetyl-2-aeety uo-n, N-diä yl-benzylamin: Sehmelzpunkt: 102 to 103°C. Made of 5-Acetyl-2-aeetylamino-ben ylbromid and Diä hylamin similar to example 8. With spi el 9 5: 5-Acetyl-2-acetylamino-N, N-dfpropyl-benzylomln: Sehmelzpunkt: 80 to 820C. Made of 5-Acetyl-2-aeetyl ylbromid and Dipropyl n ino ben similar to example 8. B e i s p i e i 9 6: 5-Acetyl-2-acetylamino-N, N-dibutyl-b nzylamin: Sehmelzpunl: 40 to 42°C. Made of 5-Acet-yl-2-acetyl min above ylbromid and Dlbutyl in similar to example 8. Example 97: N (5-Acetyl-2-acetyln nluo benzyle) - pyrrolidin: Sehmelzpunkt: 88 to 9O°C. Made of 5-Acetyl-2-aee yl NO-benzyIbromid and Pyrrolidin similar to example 8. B e i s p i e I 9 8: N (5-Acetyl-2-aeetylamino-benzyl) - piperidin: Fusion point of the Hydrocblorids: 210 to 212°C. Made of 5-Aeetyl-2-acetylamino-benzylbromid and Piperidin similar to example 8. B e i s p i e I 9 9: N (5-Aeetyl-2-acetyl mlno benzyle) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point: 112 to 114°C. Made of 5-Acetyl-2-acetylarnlno-benzylbromid and hexadecimal hexadecimalaminehexadecimal amine similar to example S. B eispiel 1 0 0: N (5-Acetyl-2-acetyla ino benzyle) - morphelin: Sehmelzpunkt: 100 bis1020C. Made of 5-Acetyl-2-acetyl mlno bensylbromid and Mo pholin similar to example 8. B e i s p i e I 1 01: 5-Aeetyl-2-acetyl nino n cyelohexyL N METHYl benzylamin: Scb.melzpunkt of the hydrochloride: 210 bis2110C. Made of 5-Acetyl-2-acetylamino-benzylbromid and N-methyl-cyclohexy rnln similar to example 8. Example 1 02: 5-Acetyl-2-aeetyl rnino n äflayL N C'YCLOHEXYl fuel element zy rnin " fusion point: 98 to 100°C. Made of 5-Acetyl-2-acetylamino-benzylbromid and N-Äf yl-cyclohexyl n similar to example 8. B e i s p i e i 1 0 3: 5-Acetyl-2-Acetylen-N-cyclohexyl-N-isopropyl-ben ylamin: Sehmelzpunkt: 108 to 110°C. Manufactured play 8. from 5-Acetyl-2-acetylamino-benzylbromid and N-Isopropyl-cyclohexylamtn similar to BeiB e t s p i e 1 1 0 4: N (5-Acetyl-2-aeetylamino-benzyl) - N' - methyl piperazin: Fusion point of the Dihydrochlorids: starting from 275°C (Zers.). Made of 5-Acetyl-2-aeetylsmino-benzylbromid and N-methyl-piperaztn similar to example 8. B e i s p i e 1 1 0 5: 2-Amino-Ne-isopropyl-3-trif! uormethyl benzylamin: Sehmelzpunkt of the Hydrochlorlds: 188 to 18S°C. Made of 2-Amino-3-trlfluormethyl-benzylchlorid and Isopropylamin similar to example 1. B e i s p i e I 1 0 6: 2-Amino-N, N-diäthyl-3-trlfluonnethyl-benzylamin: Sehmelzpunkt of the Hydroehlorids: 194 to 196°C. Made of 2-Amino-3-trlfluomethyl-benzylchlorld and Diäthylamin similar to example 1. B e i s p i e I 1 0 7: N (2-Amino-3-trifluonnethyl-benzyl) - hexadecimal hexadecimalaminehexadecimal amine: Sehmelzpunkt of the Hydrocblorids: 208 to 9.09°C. Made of 2-Amino-3-trlfluormethyl-benzylchlorid and Hexamethylenamln similar to example 1. With play 1 0 8: N-Äthyl-2-amino-N-oyclohexyl-3-trifluonnethyl-benzylamin: Sehmelzpunkt of the Hydrochlo ids: 189 bis191°C. Made of 2-Amino-3-trifluormethyl-benzylchlorld and N-Äthylcyclohexylamin similar to example 1. B e i s p i e I 1 0 9: 2-Amino-N-methyl-N (morphollno carbonyl methyl) - 3-trifluormethyl) - benzyle amine: Fusion point of the hydrochloride: 200 to 203°C (Zers.). Made of 2-Amino-3-trlfluormethyl-benzylchlorld and Sarkosin morpholin similar to example 1. Example 1 1 0: N (2-Amino-3-brom-5-fluor-benzyl) - pyrroltdin: Sehmelzpunkt of the Dihydrochlorlds: 173 to 175°C (Zers.). Made of 2-Amino-3-brom-5-fluor-benzy alkuhel, Thionylchlorid and Pyrrolldin similar to play i. Example 1 11: 2-Amino-3-brom-5-fluor-N (trans-4-hydroxy-oyelohexyl) - benzyle amine: Sclunelzpunk of the Hydrochlorlds: 237 to 239°C (Zers.). Made of 2-Binino-3-brom-5-fluor-benzylalkohol, Thionylcblorld and trans-4-Hydroxy-cyclohexylamin änalog example 1. B e i s p i e I 1 12: 2-Acetamino-5-carbomethoxy-N, N-diäthylben ylamin. 3, 4 g 2-Aeetamino-5-carbomethoxy-benzylbromid are solved in 125 ml chloroform and let after addition from 85 ml Diäthylamin 15 min stand. One restricts those in the vacuum to the Troclme, takes up the Rüokstand to chloroform, vibrated CH! oroforrnlösur with diluted hydrochloric acid out,] night the wYmsertge phase with ammonia alkalinely and vibrates again with chloroform out. This chloroform excerpt is dried over Natriumsalfat and restricted in the vacuum. The arrears are 2-Acetamlno-5-carbomethoxy-N, N-diäthyl-benzylamin (Sehmelzpunkt: 77 to 80oc) and one transfers with methanolic hydrochloric acid into the Hydroohlorid by the Schmelzpunkt' 213 to 214°C. B e i s p i e 1 1 1 3: 2-Amino-5-brom-N, N--dimethyl-3-fluor-benzylamin: 5, 5 g 2-Amino-5-brom-3-fluor-bonzylalkohol are solved in 150 Al chloroform. Under agitating and cooling with ice one admits drop by drop Thionylchlorid to 7.13 g (4, 35 valley), whereby a yellow precipitation fails. One leaves the suspension untouched at ambient temperature over power and confines then prays ambient temperature at the rotation evaporator to the Trockue in. In such a way won raw Benzylehlorld is suspended in 150 ml chloroform. Under agitating and cooling with ice one gives hiezu 20 ml D [methylamin, whereby a clear solution will receive. One leaves 30 untouched min under ice cooling and extracts then twice with satisfied potassium carbonate solution. The chloroform phase is washed with water, getroeknet over Natrinmsulfat and evaporated in the vacuum to the Trookne. The arrears are taken up in absolute ethanol and acidified with ätherlscher hydrochloric acid to pH 3. The failed Hydrochlorld is sucked off and solved in absolute ethanol. After additive of activated charcoal the solution is heated up for simmering. One receives colorless crystals to Mach filtering the activated charcoal off and after additive of ether from the fusion point 263 to 265 C (Zers.). B e i s p i e 1 1 14: 2-Amino-5-brom-N-cyclohexyl-3-fluor-N-methyl-henzylamin: Fusion point of the hydrochloride: 226 to 228°C (Zers.). Made of 2-Amino-5-brom-3-fluor-benzylalkohol, Thiony [ehloßd and N-methyl-eyelohexylamin similar to example 113. B e i s p i e 1 1 1 5: 2-Amino-5-brom-N (trans-4-hydroxycyclohexyl) - 3-fluor-benzylamin: Sehmelzpunkt of the hydrochloride: 231 to 9.33°C. Made of 2-ArnJno-5-brom-3-fluor-benzylalkohol, Thionylchlorld and trans-4-Hydroxy-cyelohexylamin similar to example 113. B e i s p i el 1 1 6: N-Äthyl-2-arn no-S-brom-N-eyclohexyl-3-fluor-benzylamin: Fusion point of the Hydroehlorids: 193 to 195°C. Made of 2-Amino-5-brom-3-fluor-bonzylalkohol, Thionylehlorld and N-ethyl-cyclohexylamin similar to example 113. B e i s p i e 1 11 7: 2-Ace mino-5-brom-N, N-dimethyl-3-dimethylamino-methyl-benzylamin: 12 g 4-Brom-2, 6imethyl-acetanilid are solved in 1, 9 1 Tetraehlomethan and heated up for simmering. One illuminates the solution with UV light and drips within 50 in 15, 8 g bromine too. After cooling on space temp advice r one admits 60 ml Dimethylamin and leaves untouched over night. One vibrated twice with water out, more dryly over NatriumsaIfat and restricts in the vacuum to dry ones. The arrears are solved in ethanol and the solution with äthanolischer hydrochloric acid is acidified; it crystallizes 2-Acetamino-5-brom-N, N-dimethyl-3-dimethyls ino methyl benzylamin dihydrochlorid from the Sehmelzpunkt 2910C (Zers.). B e i s p i e 1 11 8: 4-Brom-2, 6-bis (pyrrolidino methyl) - acetanilid: Schmelzpunk of the Dihydrochlorids: 319°C (Zers.). Made of 4-Brom-2, 6-dimethyl-acetanilid, bromine and Pyrrolidin similar to example I17. B e i s p i e I 1 1 9: 4-Brom-2, 6-bis (piperidino methyl) - ace anilid: Fusion point of the Dihydrochlorids: 308 to 312°C (Zers.). Made of 4-Brom-2, 6-dimethYl-acetaniHd, bromine and Piperidin similar to example 117. Example 120:4 - bromine: 2,6-bis (morpholino methyl) - acetanilid: Fusion point of the Dihydrochlorids: 283 to 284°C (Zers.). Made of 4-Brom-2, 6-dimethyl-acetanilid, Brmn and Morpholin similar to example 117. B e i s p i e 1 1 21: 5-Acetyl-2ino-3-brom-N (trane-4-hydroxycyelohexyl) - benzyle amine: Fusion point of the hydrochloride: 214 to 2160C (Zers.). Made of 5-Acetyl-2-amino-3-brom-banzylbromid and trans-4-Hydroxy-eyeIohexylamin similar to example 112. B e i s p i e 1 1 2 2: 5-Acetyl-2” no-3-ch! Or-n (trans-4-hydroxyeyclohexyl) - benzyla in: Fusion point of the hydrochloride: 192 to 194°C (Zers.). Made of 4-Aeetamino-2-amlno-3-chlor-benzylbromid and trans-4-HydroxycycIohexylamin similar to example 112. B e i s p i e 1 1 2 3: 2-A ino n [1, 3-dihydroxy-2-methyl-propyl (2)] - 3-trifluormethyl-benzylamin: Sehmelzpunkt: 110 to 112oc. Made of 2-Arnino-3-trifluormethyl-benzylchlorid and 2-Amino-2-methyl-1, 3-propandiol similar to example 112. Example 124:2 - Arn NO-n (cis-3-hydroxy-cyclohexyl) - 3-trifluormethyl-benzylamin: Sehmelzpunkt of the Hydroehlorids: 196 bis200°C. Made of 2-Amino-3-trifluormethyl-benzylchlorid and eis-3-Hydroxy-cyelohexylamin similar to example 112. B e i s p i e 1 1 2 5: 2-Amino-N (trans-4-hydroxy-cyclohexyl) - 3-trifluormethyl-benzylamin: Sehmelzpunkt of the Hydroehlorids: 228 to 230°C (Zers.). Made of 2-Amino-3-trifluormethyl-benzylehlorid and trans-4-Hydroxy-cyelohexy] amtn similar to example 112. B e i s p i e 1 1 2 6: 2-Amino-N (hydroxy tert. butyl) - 3-trifluormethyl-benzylamin: Fusion point: 110 to 1120C. Made of 2-Amino-3-trifluormethyl-benzyIchlorid and Hydroxy tert. butylamin similar to example 112. B e i s p i e 1 1 2 7: N (2-Aeetamino-5-carbäthoxy-benzyl) - pyrrolidin: Oil, chromatographisch uniformly. Made of 2-Aeeta no-5-earbäthoxy-benzylbromid and Pyrrolidin similar to example 112. B eispiel 1 2 8: 2-Acetamino-N-benzyl-5-earbäthoxy-N-tert. butyl benzyla in: Sehmelzpunkt of the hydrochloride: 2080C (Zers.). Made of 2-Aeet m no-5-carbä hoxy benzylbromid and N-tert. Butyl] - benzylamln similar to example 112o B e i s p i e 1 1 2 9: 2-Aeetamino-N-ben yl-5, N-dime ayl benzylamin: The substance is an oil; Structural proof by UV, NMI - and IR spectra. Made of 2-Aeetamino-5-methyl-benzylbromid and N-methyl-benzyla in similar to example 112. B e i s p i e I 1 3 0: 2-A ùo-3-brom-N (trans-4-hydroxy-cyelohexyl) - 5-methoxy-benzylamin: Amorphously, Struk lrbeweis by IR, UVund NMlt spectra. Made of 2-Amino-3-brom-5-methoxy-benzylalkohol, Thlonylch [orid and trans-4-Hydroxycyclohexylamin similar to example 113. B e i s p i e 1 1 31: N-Äthyl-2-a tno-3-brom-N-cyelohexyl-5-methyl-benzylamin: 4, 4 g 2-Amino-3-brom-5-methyl-benzylslkohol are heated up with 1, 5 g Propionsäure and 3 g N-ethyl-cyclohexylamin 5 h auf1650C. One restricts in the vacuum to the Troekne, takes the arrears in ethers up, vibrated twice with water through, dries up, closely in the vacuum to dry ones and cleans the arrears by chromatography at silicagel (FUeßmitteI: Chloroform ethyl acetate = 6: 1). The Eluat is restricted, taken up to isopropanol and brought with Cblorwasserstoff the Hydrocblorid from the Schmelzpunkt184 to 186°C to the crystallization. B e i s p i ₜ 1 1 3 2: N-Äthyl-2-amino-3-brom-5-carboxy-N-cyclohexyl-benzylamin: 1 g 2-ATaiùo-3-brom-5-earboxy-benzylalkDhol with 3 g N-ethyl-eyclohexylamin and 1.5 gButtersäure 5 h on 140°C are heated up. One restricts in the vacuum and cleans the arrears by Chromatograpbte at silicagel with methanol as Fliefänittel. From the Eluat one receives the Hydrochlorld with hydrochloric acid from the Schm¢lzpunkt 227 to 229°C (Zers.). B e i s p i e i 1 3 3: 2-Amino-3-brom-5-carbäthoxy-N, N-diäthyl-benzylamin: 2, 7 g 2-Amino-3-brom-5-earbäthoxy-benzylalkohol are heated up with 3 g Diäthylamin and 2 g butter acid in autoclaves 5 h on 150oc. One eugt in the vacuum and cleans the arrears by Chrornatographie at silicagel with toluol/Aeeton = 4: 1 as Fließmitbsl. From the Eluat one receives the hydrochloride with ethereal hydrochloric acid from the fusion point 165 to 168°C. B e i s p i e I 1 3 4: N-ÄthyI-2-amino-3-brom-5-earboxy-N-cyclohexyl-benzylamin: 2.4 g 2-Amino-3-brom-5-carboxy-benzylalkohol are heated up with 3, 3 g N-ethyl-cyelohexylamin and 0.1 g magnesium oxide 5 h on 150°C; subsequently, the received product 7wischen chloroform and water is distributed, the chloroform phase is dried and restricted to dry ones. By taking up the arrears to ethanol and addition of ethereal hydrochloric acid the hydrochloride is brought by the Scb_melzpunkt 227 to 229°C (Zers.) to the crystallization. Example 135:2 - Amino-3-brom-5-carbäthoxy-N, N-diäthyl-benzylamin: 2.7 g 2-Amino-3-brom-5-earbäthoxy-benzylalkohol are heated up with 2,4 g Diäthylumin and 0, 2 g magnesium oxide in autoclaves 5 h to 150 bis160°C. One restricts the arrears with toluol acetone (4 in the vacuum and chromatographiert: 1) at silicagel. From the Eluat one receives the Hydroehlorid with ethanol/hydrochloric acid from the Sckmelzpunkt 165 to 168°C. Example 136: N-Äthyl-2-amino-3-brom-5-earboxy-N-cyelohexyl-benzylamin: 2, 5 g 2-Amour-3-brom-5-earboxy-benzylalkohol are heated up with 4 g N-ethyl-cyclohexylamin and 0.1 g sulfuric acid 5 h on 150°C. One distills the surplus N-ethyl-cyelohexylamin in the vacuum off and distributes the arrears between chloroform and diluted ammonia. The chloroform solution is getrockuet and restricted to the Troekne; the arrears are chromatographlert at silicagel with methanol and brought from the Eluat by ethereal hydrochloric acid the Hydroehlorld by the Sehmelzpunkt 227 to 229°C (Zers.) to the crystallization. B egg spi el 1 3 7: 2-Amino-3-brom-5-carbäthoxy-N, N-diäthyl-benzylamin: 2, 7 g 2-Amino-3-brom-5-carbäthoxy-benzylaikohol are heated up with 2,4 g Diäthylamin and 0.1 g sulfuric acid in autoclaves 5 h to 150 to 160°C. One restricts chromatography at silicagel with toluol acetone (4 in the vacuum, distributes the arrears between chloroform and diluted ammonia, restricts the chloroform solution and cleans the Ritckstand duroh: 1) as flow materials. From the Eindampfrüekstand of the Eluates one receives the hydrochloride with äthanolis cher hydrochloric acid from the fusion point 165 to 1680C. B e i s p i e 1 1 3 8: N-Äthyl-2-amino-3-brom-5-carboxy-N-eyelohexyl-benzylamin: 2, 9 g 2-Aeetamino-3-brom-5-earboxy-benzylalkohol are agitated with 1,5g N-ethyl-cyelohexylamin in 20 ml tetralin 4 h with 175°C. One restricts the solution in the vacuum to the Trockue, distributes the arrears between chloroform and water, eugt the chloroform solution to the Trockue and chromatographiert the arrears at silicagel with methanol. From the Eluat one receives the Hydroeblorid by addition from ethereal hydrochloric acid from the fusion point 227 to 229°C (Zers.). B e i s p i e 1 1 3 9: 2-Amino-3-brom-5-carbäthoxy-N, N-dtäthyl-benzylamin: 3.1 g 2-AcetaTaiuo-3-brom-5-carbäthoxy-benzylalkohol are heated up with 2,4 g Diäthylamin in autoclaves 5 h to 150 to 17 0°C. One eugt and chromatographiert the arrears at silicagel with toluol acetone (4: 1) as flow materials. From the Eluat one receives the Hydroehlorid with äthanoliseher hydrochloric acid from the fusion point 165 bie168°C. B e i s p i e i 1 4 0: 2-Amino-3-brom-5-earbäthoxy-N, N-diäthyl-benzylamin: 1 g 3-Acetoxymethyl-4-amino-5-brom-benzoesäureäthylester is heated up in autoclaves 2 h with 5 mI Di hylamin on 120°C. After cooling on ambient temperature the reaction mixture in the vacuum is restricted to dry ones and the arrears by Chrornatographie at gravel elgel (Fließmitteh ToluohAceton = 4: 1) cleaned. From the Eluat one receives the hydrochloride by means of hydrogen chloride from the SchmelT.punkt 165 to 168oc. B e i s p i e I 1 41: N-Äthyl-2-amino-3-brom-5-carboxy-N-cyclohexyl-benzylamin: 2, 8 g 3-Aeetoxymethyl-4-amino-5-brom-benzoesäure are heated up with 5 g N-ethyl-eyclohexylamin 5 h to 120 to 130°C. One restricts in the vacuum to dry ones and cleans the arrears by chromatography at silicagel with methanol as flow material. From the Eluat mau with ätheriseher hydrochloric acid the Hydrochiorid receives 227 to 229°C (Zers.) from the fusion point. B e i s p i e I 1 4 2: 2-Amino-3-brom-5-carbätäoxy-N, N-diäthyI-benzylamin: 2.7 g 2-Amino-3-brom-5-carb thoxy benzylalkohol and 0.5 g sodium hydride are cooked for absolute ether and 50 in 100 ml ml absolute Tetmhydrofuran 6 h. One läiblt on -70°C off, admits slowly to 1, 7 g ToluoIsulfochlorid into 30 ml ethers, lets the mixture under agitating to -30Oc warm up, cools -70°C down and admits 1.4 g Diäthylamin. The KühIbad is removed and the mixture is agitated, until it reached Raumtemperatut. One vibrated with water, sennt the organic phase off, restricts her in the vacuum and chromatographiert denRückstand anIfäeselgeI with ToIuol! Aceten (4: 1). From the Eluat one receives the hydrochloride with hydrochloric acid from the fusion point 165 to 168°C. B e i s p i e 1 1 4 3: N-Äthyl-2-sm e-3-brom-5-carbexy-N-cyclohexyl-benzyl nin: 3.2 g (2-Anno-3-brom-5-carboxy-benzyl) - thylester and 13, 7 g N-ethyl-cyclehexylamin are heated up in presence of sourer alumina 5 h on 200oc. The reaction mixture is distributed afterwards between water and Chlorofom, the Chleroformphase is washed, getroctmet and restricted with water. The arrears are chromatographiert at silicagel with methanol. From the Eluat one receives the Hydrocblorid with hydrochloric acid from the Sclnnelzpunkt 227 to 229°C (Zers.). Example 144:2 - ATù ùo-3-brem-5-caxbäthexy-N, N-diäthyl-benzyla, n: 3.5 g (2-Amine-3-brom-5-canbäthox y-benzyle) - phenyI ethers and 6 ml Diäthylamin heated up in autoclaves in present ven sourer alumina 5 h to 180 to 200OC. One restricts, distributes the arrears between chloroform and water, the dry chloroform phase, restricts her and chrcmatographtert the arrears at KieselgeI with toluol acetone (4: 1), from which Eluat receives, ù n with äthanelischer hydrochloric acid the Hydrechlorid of the fusion point 165 to 168ec. B e i s p i e I 1 4 5: N-ÄthyI-2niuo-3-brom-5-carbexy-N-cyclohexyI-benzylamin: 4.7 g n (2-Amino-3-brom-5-carboxy-benzyI) - N, N-diäthyl-methyla oniumjodid with 10 g N-ÄthyI-cyclehexylamin 1 h on 150°C heat up one distills the surplus N-ethyl-cyclohexyl ntn in the vacuum off and distributes the arrears between chloroform and diluted ammonia. The chloroform phase is washed, restricted with water and übergefiihrt derRückstaud by release in ÄthanoI and addition from ethereal Salzsänre into the Hydrochiorid by the fusion point 227 to 229°C (Zers.). B e i s p i e 1 1 4 6: 2-ATnino-3-brem-5-carbäthoxy-N, N-diäthyl-benzylamin: 4.4 g n (2-A,}, o-3-brom-5-carbäthoxy-benzyI) - trimethyl A, rnoniumjodid are heated up with 10 gDiäthylamin in autoclaves the 1 h to 150 to 1700C. One restricts de Rückstand between ChIoreform and water in the vacuum, distributed, restricts the chloroform solution and chromategraphiert the arrears at silicagel with TeluoI/Acet n (4: 1) as Fließmißel.Aus one receives the hydrochloride to the Eluat with äthanolischer hydrochloric acid from the Sekmelzpunkt 165 to 168°C. B e i s p i e 1 1 4 7: N (2-Amino-5-carbox y-benzyle) - hexadecimal hexadecimalaminehexadecimal amine: Fusion point of the Dihydrochlorids: starting from 121oc (Zers.). Made of 2-A {- o-5-carboxy-benzylbremid and Hex ethyl amine similar to example B egg FR i el 1 4 8: 2-Ansko-3-brom-5-carbä hoxy n cyclohexyL N METHYl benzylamin: Fusion point of the Hydrochlerids: 212 to 2159C. Made of 2-_4, ni, o-3-brom-5-carbäthoxy-benzylbromid and N-methyl-cyclohexylamin similar to example example 149:2 - to {, e-3-brom-5-carbäthox y-n (traus-4-hydrox y-cyciohexyl) - benzyle amine: Fusion point of the hydrochloride: 1370C (Zers.). Made of 2-Ahne-3-brom-5-carbäthox y-benzylbromid and trans-4-Hydrox y-cyclohexylaminanalog example B e i s p i e 1 1 5 0: N (2-A no-3-brem-5-carb äthoxy benzyI) - hexamethylen ù n " fusion point of the HydrochIorids: 219 to 221°C. Made of 2-An-o-3-brom-5-carb hoxy benzylbremid and hexane ethyl amine similar to example B e i s p i e 1 1 51: N-ÄthyI-2-amino-N-cyclohexyt-5-methyl-benzylamin: Schmelzpuntd of the hydrochloride: 189 to 191eC (Zers.). Made of 2-Ano-5-methyl-benzylbromid and N-ethyl-cyclohexylamin similar to example example 152:2 - at the o-3-brom-5-cyan-N-cyclohexyl-N-methyl-benzyI” fusion phase of the hydrochloride: 236 to 240ec. Made of 2-Amino-3-hrom-5-cyan-benzylbromid and N-methyl-cyclohexylamin similar to example B e i spi el 1 5 3: 2-Amine-3-brom-5-carbamoyl-N, N-diäthyl-benzylù: Fusion point: 140 to 142°C. Made of 2-Anno-3-brem-5-carbamoyl-benzylbremid and Diäthylamin similar to example B e i s p i e 1 1 5 4: 2 - At the ne-5-brom-N, N-diäthy1-3-trifluormethyl-benzylamin: Schmelzpankt of the Hydrocblorids: 198 to 200°C. Made of 2-Autor-5-brom-3-trifluormethyl-benzylbromid and Diäthylamin similar to example B e i s p i el 1 5 5: 2-Amino-5-brom-N, N-diäthyl-3-methyl-benzyl.amin: Sclnnelzpankt of the Hydroc lorids: 177 to 179°C Zers. ). Made of 2-Amino-5-brom-3-methyl-benzylbromid and Dfä hylamin similar to example B el s p i e I 1 5 6: N-Ä hyl-2-amino-5-brom-N-cyclohexyl-3-methyl-beazylamin: Sehmelzpunkt of the Dihydrochlorids: 183 to 187°C (Zers.). Made of 2-Amino-5-brom-3-methyl-benzylbromid and N-ethyl-eyclohexylamin similar to example B e i s p i e T1 5 7th n (2-Amino-5-brom-3-methyl-benzyl) - hexamethylenamim boiling point of the Dihydrochlorids: 159 to 164°C (Zers.). Made of 2-Amino-5-brom-3-methyl-benzylbromid and hexadecimal hexadecimalaminehexadecimal amine similar to example B e i s p i e 1 1 5 8: 2-Amtno-5-brom-4-tert. butyl n cyclohexyL N METHYl benzylamim fusion point of the Hydroehlorids. 202 to 202, 5°C (Zers.). Made of 2-Amino-5-brom-4-tert. butyl benzylbromid and N-17Iethyl-cyclohexylamin similar to example example 159: N (2-Amino-5-brem-4-tert. butyl benzyle) - morpholin " fusion point of the Dihydrochlorids: 194 to 198°C (Zers.). Made of 2-Amino-5-brom-4-tert. butyl benzylbromid and Morpholin similar to example i0. B el FR i el 1 6 0 • 2-Arnino-5-brom-N (trans-4-hydroxy-cyclohexyl) - N-methyl-3 [N-methyl (tran -4 - - hydroxy cyclohexylamino) - methyl] - benzyle amine. Fusion point: 179 to 180°C. Made of 2-Amino-5-brom-3-hydroxymethyl-benzylalkohol, Thionylehlorid and N-methyl-trans -4 " hydraulic XY cyclohexyl amine similar to example 1. B e i s p i e I 1 61 • 2-Amino-3-brom-N, N-dimethyl-5-methoxy-benzylamin: Oil, structural proof by IR, UVund NMR spectra. Made of 2-Amino-3-brom-5-methoxy-benzylbromid and Dimethylamin similar to example i0. B e i s p i e I 1 6 2: N (5-Aeetyl-2-amino-ben yl) - hoxamethylenamin: Sehmelzpunkt of the IIydroehlorids: 205 to 207°C (Zers.). Made of 5-Acetyl-2-amino-benzylbromid and hexadecimal hexadecimalaminehexadecimal amine similar to example B e i s p i e 1 1 6 3: 5-Acetyl-2-amino-3-brom-N, N-dimethyl-benzylamin. Fusion point: 92 to 95°C. Made of 5-Acetyl-2-amino-3-brom-benzylbromid and Dimefl ylamin similar to example B ₜ i s p i el 1 64: 5-Aee yl-2-amfno-N, N-dimethyl-benzylamta: Fusion point of the Hydroehlorids: 209 to 21sec (Zers.). Made of 5-Aeetyl-2-amino-benzylbromid and Dimethylamin similar to example example 165: N-Äthyl-2-amino-3-brom-N-cyclohexyl-5 (1-hydroxyäthyl) - benzyle amine: Fusion point: 117 to 121°C. Made of 2-Amino-3-brom-5 (1-hydroxyäthyl) - benzyle bromide and N-ethyl-eyclohexylamin similar to example B e i s p i e 1 1 6 6: 2-Amino-3-brom-5-carbäthoxy-N, N-< left ithyl benzylamin: Fusion point of the hydrochloride: 165 to 168°C. Made of 2-Amino-3-brom-5-earbäthoxy-benzyl-pyrldiniumbromid and Diäthylamin similar to example 146. B e i s p I e 1 1 6 7: N-Äthy1-2-amino-3-carboxy-N-cyelohexyl-benzylamin: Fusion point of the Hydrochlorlds: 193 to 1970C. Made of 2-Amino-3-carboxy-benzylbromid and N-Äthylcyclohexylamin similar to example B e i s p i e 1 1 6 8: N-Äthyl-2-amino-5-brom-3-carboxy-N-cyclohexyl-benzylamin: Fusion point of the hydrochloride: 130 to 140°C. Made of 2-Amino-5-bzom-3-carboxy-benzylbromid and N-Äähylcyelohexylamtn similar to example example 169:2 - Acetamino-3-brom-N, N-diäthyl-5-methyl-benzylamin: 1, 53 g 2-Amino-3-brom-N, N-diäthyl-5-methyl-benzylamin-hydrochlorid in 50 ml Aeetanhydrid bei75°C is solved. One evaporates in the vacuum to the Troekne and recrystallizes the arrears from ethanol. The received 2-Acetamino-3-brom-N, N--diäthyl-5-methyl-benzylamin-hydrochlorld melts bie 172°C with 170. B e i FR i e 1 1 7 0: 2-Acetamino-3-brom-N, E-dimethyl-n (trans--4-hydroxyeyelohexyl) - benzyle amine: 2.2 g 2-Amino-3-brom-N, 5-dimethyl-N (trans-4-hydroxycyclohexyl) - benzyle amine are solved in 100 ml methanol and heated up for simmering. In the course of 2 h one adds ml acetic anhydride to 75 and distills thereby the developing acetic acid methyl ester off. One evaporates in the vacuum to the Troekae and repeats after additive of further methanol evaporation. The received Rlickstand is solved in ethanol and with ä hanoäscher hydrochloric acid into dae 2-Acetawir o-3-brom-N, 5-dimethyl-N (trans-4-hydroxycyclohexyI) - benzyla nin hydrochloride transfers. Sehmelzpunkt: 246 to 248°C. B e i s p i e i 1 71: 3-Brom-2-butyrylamino-5-earbä hoxy n, N-diäthyI-benzylamin: 3 g 2-Arnino-3-brom-5-carbäthoxy-N, N-diäthyl-benzyle rn n is solved in 30 ml benzene and warmed up with 3 ml Bußersäurecblorid 30 min to 50oc. One restricts in the vacuum to dry ones and cleans the arrears by chromatography at silicagel (Fließmitteh BenzohEssigester = 6: 1); one receives - but-yrylino-5-carbäthoxy-N, N-diäthyl-benzylamin, which is transferred with äthanoliseher hydrochloric acid into the hydrochloride by the fusion point 134°C to 3-Brom-2. B e i s p i e 1 1 7 2: 2-Aeete no-3-brom-5-carbäthoxy-N-cyclohexyI-N-methyl-benzylamin: Fusion point of the hydrochloride: 220 to 223°C. Made of 2-Amino-3-brom-5-carbäthoxy-N-eyclohexyt-N-methyl-benzylamin and Acetylehlorid anaIog example 171.