Syntheses of Ammonium Compounds Containing Diphenyl Ether Nucleus

In order to test the curare-like action, following three ammonium compounds possessing diphenyl ether as the functional group were prepared: 4, 4′-bis(Dimethylamino)-diphenyl ether dimethiodide (II), 4, 4′-bis(dimethylaminomethyl)diphenyl ether dimethiodide (III), and 2-methoxy-5, 4′-bis(dimethylaminomethyl)diphenyl ether dimethiodide (IV). For comparison, 4, 4′-bis(dimethylaminomethyl)biphenyl dimethiodide (V) was also prepared. For their preparation, diphenyl ether, 2-methoxydiphenyl ether, or biphenyl was derived to bis(chloromethyl) or a corresponding bromo derivative to which was applied liquid dimethylamine. Methyl iodide was then applied to the dimethylaminomethyl derivatives thereby formed to the corresponding objective compounds.