Studies on the syntheses of analgesics. VI. Synthesis of 1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine derivatives.

Abstract

Continuing our study of new types of non-narcotic analgesics, we synthesized several 1, 2, 3, 4, 5, 6-hexahydro-6, 6-dimethyl-1, 5-methano-3-benzazocine derivatives from ethyl 4-methoxyphenylacetate via the ring closure reaction of 5-(1-hydroxy-1-methylethyl)-3-(4-methoxyphenyl)-2-piperidinone (V). The by-product which was produced by the ring closure reaction of V, was presumed to be 1, 2, 3, 4, 5, 6-hexahydro-8-methoxy-6, 6-dimethyl-9-sulfo-1, 5-methano-3-benzazocine (VII). The synthesized compounds were tested for analgesic activity in mice.