Studies on the Syntheses of Analgesics. V. Synthesis of 1, 2, 3, 4, 5, 6-Hexahydro-3-benzazocine Derivatives. (3)

Abstract

Continuing our study on new types of non-narcotic analgesics, we synthesized 1, 2, 3, 4, 5, 6-hexahydro-8-methoxy-6, 6-dimethyl-3-benzazocine (XI) from 2-(2-cyano-1, 1-dimethylethyl)-4-methoxybenzoic acid, through 3-(2-cyanomethyl-5-methoxyphenyl)-3-methyl-butyronitrile (X). The reductive ring closure reaction of X was particularly investigated to obtain XI and the pathway of this reductive ring closure reaction was estimated from the reactivity of the by-products, 3-[2-(2-aminoethyl)-5-methoxyphenyl]-3-methylbutyronitrile and 3-[2-(2-aminoethyl)-5-methoxyphenyl]-3-methylbutylamine.