Ethyl 1-cyanocyclohexane-1-carboxylate → Ethyl 1-(aminomethyl)cyclohexane-1-carboxylate

Participants

Reaction Steps

Platinum (IV) oxide (1.72 g) was added to a solution of ethyl 1-cyanocyclohexanecarboxylate (17.15 g, 94.6 mmol) in concentrated hydrochloric acid (20 mL) and ethanol (200 mL), and the mixture was placed under hydrogen pressure on a Parr apparatus and shaken for 20 hours. The solvent was removed under reduced pressure, and the residue was diluted with water. The resulting mixture was adjusted to pH 7 with the addition of solid sodium carbonate and then extracted several times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 5.67 g of ethyl 1-(aminomethyl)cyclohexanecarboxylate as a colorless oil. A portion of the water was removed from the aqueous layer, and dichloromethane was added. The mixture was stirred overnight at ambient temperature, and the organic fraction was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.69 g of ethyl 1-(aminomethyl)cyclohexanecarboxylate hydrochloride as a white solid.

Provenance & Evidence