2,2-Diphenylpropylamine → N-(2,2-diphenylpropyl)-2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetamide

Participants

Reaction Steps

To a solution of 2,2-diphenylpropan-1-amine (0.10 g, 0.5 mmol) in dichloromethane (10 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.16 g, 0.50 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.19 g, 1.00 mmol) and N,N-dimethylpyridin-4-amine (6 mg, 0.05 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 (1:3) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.05-7.35 (m, 20H), 6.0-6.1 (m, 1H), 3.98 (s, 2H), 3.95 (s, 2H), 3.2-3.4 (m, 2H), 2.4-2.5 (m, 2H), 1.65-1.75 (m, 2H), 1.5 (s, 3H); MS (ESI+) m/z 503 (M+H)+.

Provenance & Evidence