Derivatives of 10,11-dihydro-5h-dibenzo(a,d)cycloheptene and related compounds. V. Homologous 4-azaketones and derivatives

6,7-Benzo-12H-5,6,7,12-tetrahydrocycloocta[1,2b]pyridine-12-one (III) and 5,6-benzo-5,6,11,12-tetrahydrocycloocta[1,2b]pyridine-11-one (IV) were prepared. Wolff-Kishner reduction gave the corresponding azahydrocarbons (VIIa and IX). Alkylation of 6,7-benzo-12H-5,6,7,12-tetrahydrocycloocta[1,2b]pyridine, using potassium amide and liquid ammonia, gave the corresponding 12-dialkylaminoalkyl derivatives (VIIb and VIIc). The dehydration of 12- hydroxy - 12 - (1 - methyl - 4 - piperidyl) - 6,7 - benzo - 12H-5,6,7,12-tetrahydrocycloocta[1,2b]pyridine (V), prepared by two methods, gave 4-aza-4b-(1-methyl-4-piperidyl)-9,10-dihydroindeno[1,2a]indene (VI). The compounds were without significant biological activity.