Abstract
In order to test the analgesic action of azabenzomorphane derivatives, 4-benzyl-3, 4, 5, 6-tetrahydro-1 H-2, 6-methanobenzo [e][1, 3] diazocine (XVIa) and its 2-phenyl derivative (XVIb) were synthesized by cyclization of 4-(benzylaminomethyl)-1, 2, 3, 4-tetrahydroisoquinoline with paraformaldehyde and benzaldehyde. Both compounds were found to be extremely lavile ahainst acid. Methods for synthesis of VI, which was used as a key intermediate, were also examined using 4-cyanoisoquinoline (II) as a srarting material according to three procedures, namely, a) catalytic hydrogenation of 4-benzylaminoisoquinoline (IV), b) reduction of 4-(benzamidonethyl) isoquinoline (X), and c) hydrogenation of the cyclization product between 4-aminomethyl 1-1, 2, 3, 4-tetrahydroisoquinoline (XV) and benzaldehyde.
