4-Benzhydrylpiperidine → HCID 57402040, compound

Participants

Reaction Steps

To a solution of 4-benzhydrylpiperidine (0.13 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 7.15-7.34 (m, 20H), 4.52-4.60 (m, 1H), 4.27 (d, J=15.7 Hz, 1H), 4.11 (d, J=15.7 Hz, 1H), 3.64-3.76 (m, 1H), 3.45-3.50 (m, 3H), 2.93-3.02 (m, 1H), 2.54-2.65 (m, 3H), 2.20-2.44 (m, 1H), 1.78-1.87 (m, 2H), 1.55-1.65 (m, 2H), 1.00-1.20 (m, 2H).

Provenance & Evidence