Benzoic Acid → HCID 69058691, compound

Participants

Reaction Steps

To a solution of 3-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propan-1-amine (80 mg) prepared as described herein, dissolved in 2 mL dichloromethane, was added benzoic acid (67.6 g), 1,3-dicyclohexylcarbodiimide (68.4 mg), 4-dimethylaminopyridine (18 mg) at room temperature. After 2 hours, more dichloromethane was added and the mixture was filtered. The filtrate was concentrated onto silica gel and purified through a column (Hexane/EtOAc, 10:6-10:7), to give N-(3-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propyl)benzamide (95 mg). Demethylation as described herein gave N-(3-(6′-hydroxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propyl)benzamide (62.4 mg, Hexane/EtOAc, 10:12 as a light yellow oil.

Provenance & Evidence