4-Benzhydrylpiperidine → HCID 67359058, compound

Participants

Reaction Steps

To a solution of 4-benzhydrylpiperidine (0.25 g, 1.00 mmol) in dichloromethane (20 mL) was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) under nitrogen. To the reaction was added N1-(ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (6.1 mg, 0.005 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated, and the residue was partitioned in ethyl acetate:water (8:2). The organic layer was separated, washed with water and then brine, dried over MgSO4, 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 7.14-7.39 (m, 20H), 4.23-4.31 (m, 1H), 4.19 (d, J=16.5 Hz, 1H), 4.08 (d, J=16.3 Hz, 1H), 3.73-3.80 (m, 1H), 3.58 (d, J=11.0 Hz, 1H), 3.35 (t, J=6.7 Hz, 2H), 2.86-3.00 (m, 1H), 2.71 (t, J=6.5 Hz, 2H), 2.50-2.62 (m, 2H), 1.37-1.47 (m, 2H), 0.81-1.07 (m, 2H); MS (DCI+) m/z 529 (M+H)+.

Provenance & Evidence