Azabenzomorphane and Related Compounds. VIII. A Synthesis of 4-Benzyl-1-3, 4, 5, 6-tetrahydro-1H-2, 6-methanobenzo [e][1, 3] diazocine

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

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