Dicyclohexylcarbodiimide → 3-Dimethylamino-1,1-diphenyl-propan-2-ol

Participants

Reaction Steps

A solution of 3-dimethylamino-1,1-diphenyl-propan-2-ol (2.55 g.), 4-diethylaminobutyric acid hydrochloride (1.95 g.) and dicyclohexylcarbodiimide (2.1 g.) in dichloromethane (50 ml.) was stirred at room temperature for 5 days. Dicyclohexylurea was filtered off and the filtrate concentrated. The residue was dissolved in dilute hydrochloric acid and ether. The acid extract was basified; isolation through ether in the normal manner gave an oil which was chromatographed as alumina (200 g.). Elution with progressively graded mixtures of light petroleum and ether gave the 4-diethylaminobutyrate of 3-dimethylamino-1,1-diphenyl-propan-2-ol isolated as the dihydrochloride (41%) as a glass.

Provenance & Evidence