Abstract
Reaction of Δ1, 10-hexahydroquinolizine (I) with methyl iodide in various solvents were carried out. The reaction in the presence of methanol or ethanol proceeded at low temperature to give 10-methoxy-5-methyloctahydroquinclizinium iodide (IIIa) or the corresponding 10-ethoxy methiodide (IIIb), respectively, besides the methiodide (II). Using 70% aqueous methanol as a solvent, the reaction gave 1-methyl-6-decahydroazecinone (IV) accompanied with IIIa and II. The reaction in 70% aqueous tetrahydrofuran or aqueous acetone led to the formation of V besides II. Methiodides, IIIa and IIIb, were respectively converted into IV by heating with hydrobromic acid.
