Azabenzomorphane and Related Compounds. IX. A Synthesis of 3-Benzyl-3, 4, 5, 6-tetrahydro-2H-1, 5-methanobenzo[d][1, 3]diazocine. (Studies on the Synthesis of Heterocyclic Compounds. CXLI.)

Abstract

In order totestthe analgesic action of azabenzomorphane derivatives, 3-benzyl-3,4,5,6-tetrahydro-2H-l,5-menthanobenzo[d][1,3]diazocine and its 2-phenyl derivative were synthesized by cyclization of 3-(N-benzylaminomethyl)-l,2,3,4-tetra-hydroquinoline with paraformaldehyde and benzaldehyde. Both compounds were extremely labile against acid. Methods for synthesis of which was used as a key intermediate, were also examined using 3-cyanoquineline as a starting material according to two procedures, that is, a) reduction of 3-benzylcarbamoylquinoline and reductive benzylation of 3-aminomethyl-l,2,3,4-tetrahydroquinoline with benzaldebyde in the presence of hydrogen and platinum oxide.