Potassium Cyanide → 1-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile

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Reaction Steps

A solution of 6.0 g 1-dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) in 30 ml of dichloromethane is added to a mixture of 4.1 g potassium cyanide and 10.6 g sodium hydrogencarbonate in 30 ml of water. The resulting mixture is stirred at room temperature for 3 hours, then extracted with ethyl acetate, the organic layer dried over sodium sulfate, and the solvent evaporated. 4.8 g 1-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile is obtained. 1H-NMR (CDCl3): 3.95 ppm (s, broad, 1H), 2.90 ppm (m, 2H), 2.68 ppm (m, 2H), 2.40 ppm (s, 6H), 2.15 ppm (m, 2H), 1.95 ppm (m, 2H).

Provenance & Evidence