Studies on the Syntheses of Analgesics. XLVI. An Abnormal Hofmann Degradation of N-(4-Hydroxybenzyl)-3-benzazocinium Halides (Studies on the Syntheses of Heterocyclic Compounds. DCLXVIII)

Abstract

N-(4-Hydroxybenzyl)-3-benzazocine (II) and its similar compounds (I, III, and IV) were prepared by two routes, and selective N-debenzylation of the quaternary salts (II and III) of the benzazocines (VIII and IX) was achieved under a Hofmann degradation condition to give pentazocine (V). A normal Hofmann degradation is also described.