Studies on 1-Azabicyclo Compounds. XIX. Synthesis of Ten-membered Ring Amine Derivatives from 5-Methyl-10-nitromethyloctahydro-quinolizinium Iodide and Its Derivatives

Abstract

Reaction of Δ^{1, 10}-hexahydroquinolizine (VI) with a combination of nitromethane and methyl iodide gave 5-methyl-10-nitromethyloctahydroquinolizinium iodide (VII), which, on treatment with lithium-liquid ammonia, gave the ten-membered ring amines, XIV and XV. Similar reduction of the N-acetyl methiodide (X) and the betaine (XI) derived from VII gave XVIII and XIX, respectively.