The synthesis of several 3,4.5.6-tetrahydrobenz[b]azocin-2(1 /-/)-ones (Ill) by Beckrnann rearrangement of the oxirnes of the corresponding 1.2-benzocyclohept-I -en-3-ones (11) is described. The lactams (111) were treated with sodamide and an alkylaminoalkyl chloride in dry xylene at reflux to give 1 -alkylarninoalkyl-3,4,5,6-tetrahydrobenz[b] azocin-2 (1 H ) -ones (IV) which, on reduction with lithium aluminium hydride, afforded the corresponding 1 -alkylarninoalkyl-I ,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-alkylarninoalkyl 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.

Aus den Oximen der Cycloheptenone (I) werden über die Zwischenstufen (II) und (III) die Benzazocine (IV) (40 bis 91% Ausbeute) dargestellt, von denen verschiedene Umsetzungen angegeben werden.