Dimethylamine → (Z)-3-(4-chlorophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine oxalate

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Reaction Steps

A solution of crude 3-chloro-1-(4-chlorophenyl)-1-(3-pyridyl)-1-propene (40 mmol) was added to dimethylamine (18.0 g, 400 mmol) in 25 ml methylene chloride at 10° C. After stirring at room temperature for 1.5 h 25 ml water were added, the phases separated and the solvent removed from the organic phase. The residue was taken up in ether and extracted with dilute hydrochloric acid to pH 4.5. The aqueous phase was made alkaline, extracted with ether and the solvent removed. The residual oil (6.8 g) was dissolved in acetone and one equivalent of oxalic acid in acetone was added. The precipitated oxalate was recrystallized twice from ethanol to give 5.1 g (35%) of pure product mainly (95%) containing the Z-isomer. M.p. 164°-168° C.

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