Dimethylamine, hydrochloride → 3-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine

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Reaction Steps

To 0.25 g (1 mmol) crude 3-(4-chlorophenyl)-3-(3-pyridyl)-2-propenal, in a flask, was added in the following order: 0.73 g (9 mmol) dimethylamine hydrochloride, 10 ml methanol, 0.24 g (6 mmol) sodium hydroxide, 0.094 g (1.5 mmol) sodium cyanoborohydride and 5 g molecular sieves (3 Å). The mixture was stirred at room temperature under nitrogen for 3 days and then 100 ml methanol were added. After filtration the methanol was evaporated and the residue dissolved in a hydrochloric solution at pH 4.9 and washed with ether twice. The aqueous solution was made alkaline, extracted twice with ether and dried over MgSO4. Evaporation gave 0.18 g (66%) of pure title compound as an isomeric mixture having an approximate Z/E ratio of 54/46 (NMR).

Provenance & Evidence