N-alkylaminoalkyl derivatives of some hexahydrobenzazocines

Abstract

The synthesis of several 3,4,5,6-tetrahydrobenz[b]azocin-2(1H)-ones (III) by Beckmann rearrangement of the oximes of the corresponding 1,2-benzocyclohept-1-en-3-ones (II) is described. The lactams (III) were treated with sodamide and an alkylaminoalkyl chloride in dry xylene at reflux to give 1-alkylaminoalkyl-3,4,5,6-tetrahydrobenz[b]azocin-2(1H)-ones (IV) which, on reduction with lithium aluminium hydride, afforded the corresponding 1-alkylaminoalkyl-1,2,3,4,5,6-hexahydrobenz[b]azocines (V) in good yield. Several transformations in the 1,2,3,4,5,6-hexahydrobenz[b]azocine series are described. Some 2-alkylaminoalkyl derivatives (XIII) of the isomeric 1,2,3,4,5,6-hexahydrobenz[c]azocine, the 3-(3-dimethylaminopropyl)derivative (X) of the isomeric 1,2,3,4,5,6-hexahydrobenz[d]azocine, and 3-(3-dimethylaminopropyl)-1,2-benzocyclo-oct-1-ene (XVII) were also prepared.