Potassium Carbonate → HCID 15463127, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-phenylpiperidine (0.161 g, 1.00 mmol), (±)3-methyl-5-(4-chloro-phenyl)-pentanoic acid (0.241 g, 1.00 mol), and potassium carbonate (0.276 g, 2.00 mol) in dry dimethyl sulfoxide was heated in a sand bath (160° C.) under nitrogen for 15 hours. The mixture was cooled and diluted with water. The aqueous solution was filtered, and the filtrate was acidified with concentrated hydrochloric acid to pH=6. A brown gum formed. The liquid was decanted, and the residue was chromatographed on silica gel (38 g, 230-400 mesh) eluting with dichloromethane-methanol (20:1, 15×40 mL). Fractions containing product were combined and rotary evaporated to give a brown glass. The glass was crystallized from methanol after a hot gravity filtration to give the title compound as a tan solid; yield 0.0360 g (10%, mp=134-135° C.).

Provenance & Evidence