TRANS-OCTAHYDROPYRIDO-INDOLOBENZAZEPINES AS CENTRAL NERVOUS SYSTEM DEPRESSANTS

1449331 Octahydropyridoindolobenzazepines ENDO LABORATORIES Inc 21 Jan 1974 [22 Jan 1973 11 May 1973 6 Dec 1973 (2)] 02657/74 Heading C2C Novel octahydropyridoindolobenzazepines of the general formula n is zero or one; X is an anion of a pharmaceutically suitable acid; and R is hydrogen; 3-chloro-2-butenyl; 2-bromoallyl; benzyl; benzyl ring-substituted with methyl, methoxy or chloro; phenethyl; 3-phenylpropyl; 3-phenylpropyl ring substituted with chloro, bromo or methoxy; furfurtyl; 2-thenyl; acetonyl; phenacyl; C 1 -C 5 , alkyl; C 3 -C 5 alkenyl; C 3 -C 5 alkynyl; cinnamyl; cinnamyl ring-substituted with chloro, bromo, or methoxy; 3-phenyl-2- propynyl; cyclopropyl ; C 4 -C 8 cycloalkylmethyl (methylcyclopropyl)methyl; (cis - 2,3 - dimethylcyclopropyl)methyl; C 6 -C 8 cyclo = alkenylmethyl; C 6 -C 8 cycloalkadienylmethyl; (2,3-dimethylcycloprop- 2 - en - 1 - yl)methyl; exo - 7 - norcarylmethyl; (cis - 1,6 - dimethylendo - 3 - norcaren - 7 - yl)methyl; (4 - methylbicyclo[2.2.2]oct - 1 - yl)methyl; (4 - methylbicyclo[2.2.2]oct - 2 - en - 1 - yl) methyl; (bicyclo[2.2.1]hept - 2 - yl)methyl; bicyclo[2.2.1]- hept - 2 - en - 5 - yl)methyl; 1 - adamantylmethyl; or 2 - adamantylmethyl, and the hydrogens in the 4a and 14a positions are in trans relationship to each other, are prepared (a) when R is Ra, which is benzyl; benzyl ring- substituted with methyl, methoxy or chloro; phenethyl; 3 - phenylpropyl; 3 - phenylpropyl ring-substituted by chloro, bromo or methoxy; furfuryl; 2-thenyl; C 1 -C 5 alkyl; cyclopropyl; C 4 -C 8 cycloalkylmethyl; (methyl-cyclopropyl)- methyl; exo - 7 - norcarylmethyl; (4 - methylbicyclo[2.2.2]oct - 1 - yl)methyl; (bicyclo- [2.2.1]hept- 2 - yl)methyl; 1 - adamantylmethyl; or 2 - adamantylmethyl, by reducing with a boron hydride/tetrahydrofuran complex a hexahydro pyridoindolobenzazepine of the general formula wherein R2 is as Ra or methoxymethyl or -COR7, in which R7 is phenyl; chlorophenyl; methylphenyl; methoxyphenyl; benzylphenethyl; phenethyl ring - substituted by chloro, bromo or methoxy; 2-furyl; 2-thienyl; hydrogen; C 1 -C 4 alkyl; C 2 -C 4 alkenyl; styryl; styryl ring - substituted by chloro, bromo or methoxy; C 2 -C 7 , cycloalkyl; methylcyclopropyl; C 5 -C 7 cycloalkenyl; C 5 -C 7 cycloalkadienyl; exo - 7 - norcaryl; 4 - methylbioyclo- [2.2.2]oct - 1 - yl; bicyclo[2.2.1]hept - 2 - yl; 4 - methyl - bicyclo[2.2.2]oct - 2 - en - 1 - yl; bicyclo[2.2.1]hept - 2 - en - 5 - yl; 1 - adamantyl; or 2 - adamantyl; followed by acidification;