Studies on the Syntheses of Hydrogenated Quinolines and Isoquinolines as Analgesics. XI. Synthesis of N-Methyl-6-aza-des-N-morphinan (2-Methyl-5, 10b-trimethylene-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo [h] isoquinoline).

Abstract

Synthesis of a morphinan analog in which the ring nitrogen was transposed to 6-position has been described. A benzyl group was introduced into 5-position of 5, 6, 7, 8-tetrahydroisoquinoline, whose methohalide was reduced to the octahydroisoquinoline, and the objective compound was obtained by heating the latter in hydrobromic acid to effect rearrangement-cyclization.