Benzhydrylamine → N-benzhydryl-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

Participants

Reaction Steps

To a solution of diphenylmethanamine (0.18 g, 1.00 mmol) in dichloromethane (10 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.61 mg, 0.005 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:1) gave the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.96 (d, J=8.5 Hz, 1H), 7.21-7.37 (m, 20H), 6.13 (d, J=8.4 Hz, 1H), 4.08 (s, 2H), 3.37 (t, J=6.5 Hz, 2H), 2.71 (t, J=6.4 Hz, 2H); MS (DCI+) m/z 461 (M+H)+.

Provenance & Evidence