AMINES

摘要

1307458 1,7-Dimethyl-2-norbornanamines F HOFFMANN-LA ROCHE & CO KG 16 July 1971 [17 July 1970] 33476/71 Heading C2C Novel 1,7-dimethyl-2-norbornanamines of the general formula wherein R is a C 1-6 alkyl or optionally substituted phenyl group and R1 is a C 1-6 alkyl group, provided that at least one of R and R1 is a methyl group, and acid addition salts thereof are prepared by (a) reducing an imine of the general formula wherein R2 is a hydrogen atom or hydroxy group, or (b) hydrolysing an amine derivative of the general formula wherein R3 is a hydrolytically-removable group, and, if desired, resolving a stereoisomer or diastereomer mixture obtained and also, if desired, converting a base obtained to an acid addition salt thereof. N - [4 - (Phenyl or p-chlorophenyl) - 2 - exobornyl]-acetamide is prepared by reaction of 2- (phenyl or p-chlorophenyl)-borneol, respectively, with acetonitrile in the presence of glacial acetic acid and conc. H 2 SO 4 . N-(4-Propyl-2-exobornyl)-acetamide is prepared by reaction of 2- propylidene-camphane with acetonitrile in the presence of glacial acetic acid and cone. H 2 SO 4 . N (1,4,7;7 - Tetramethyl - 2 - exo - norbornyl) acetamide is prepared by reaction of 1-methylcamphene with acetonitrile in the presence of cone. H 2 SO 4 . N - [4 - (p - Nitrophenyl) - 2 - exobornyl] - acetamide is prepared by nitration of N - (4 - phenyl - 2 - exo - bornyl) - acetamide. N - (1,4,7,7 - Tetramethyl - 2 - exo - - norbornyl). thiocarbamic acid S-methyl ester is prepared by reaction of 1- methyl -camphene with methyl thiocyanate in the presence of glacial acetic acid and cone. H 2 SO 4 N-[4-(p-Methoxyphenyl)-2- exo.bornyl].acetamide is prepared by reaction of 2 - (p - methoxyphenyl) - bornylene - (2.) with acetonitrile in the presence of glacial acetic acid and conc. H 2 SO 4 . 2-(p-.Chlorophenyl).borneol is prepared by reaction of 4-bromo-chlorobenzene, magnesium and camphor in ether, followed by treatment of the resulting complex with ammonium chloride solution. The 1,7 -dimethyl -2-norbornanamines of the first general formula above wherein R1 is a methyl group can be reacted with 1,4-naphthoquinones of the general formula wherein X1 is a hydrogen or halogen atom or a C 1-6 alkoxy group and RX is a leaving atom or group, to give arnosebicidal and baoteriostatic 2.- bornylamino - 1,4-naphthoquinones of the general formula Pharmaceutical compositions having virucidal and anticataleptic activity comprise, as active ingredient, a 1,7-dimethyl-2-norbornanamine of the first general formula above or a pharmaceutically acceptable acid addition salt thereof together with a pharmaceutical carrier.