Cyclopropanecarboxylic acid → N-(Cyclopropylmethyl)cyclopropanecarboxamide

Participants

Reaction Steps

To a solution of cyclopropane carboxylic acid (1.72 g, 20 mmol) and cyclopropylmethylamine (1.42 g, 20 mmol) in N,N-dimethylformamide (20 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.22 g, 22 mmol) and 1-hydroxybenzotriazole (4.05 mmol, 30 mmol), and the mixture was stirred at room temperature for 20 hours. To the reaction solution was added ethyl acetate, and the mixture was washed with 1M hydrochloric acid and saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The resulting residue was recrystallized (diethyl ether-n-hexane) to give the titled compound (1.16 g, 42%).

Provenance & Evidence