Hydrochloric Acid → 1-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrile

Participants

Reaction Steps

40% aqueous dimethylamine solution (6.05 ml, 47.9 mmol) was added to a mixture of 4 M hydrochloric acid (2.61 ml) and methanol (1.56 ml), while cooling with ice. A solution of 4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanone (2.91 g, 10.0 mmol) in methanol (6 ml) and tetrahydrofuran (3 ml) was added to this mixture. Thereafter, potassium cyanide (1.56 g, 24.1 mmol) was added to the mixture, the mixture was stirred at room temperature overnight, water (150 ml) was then added and the mixture was extracted with diethyl ether (4×50 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The residue was taken up in methylene chloride (50 ml) and the mixture was washed with water (30 ml). The organic phase was dried again with sodium sulfate and concentrated i. vac.

Provenance & Evidence