Benzhydrylpiperazine → 1-[2-(4-Benzhydrylpiperazin-1-yl)-2-oxoethyl]-3,3-diphenylpyrrolidin-2-one

Participants

Reaction Steps

To a solution of 1-benzhydrylpiperazine (0.58 g, 2.30 mmol) in dichloromethane (20 mL) under nitrogen was added the product from Example 1C (0.68 g, 2.30 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.88 g, 4.60 mmol) and N,N-dimethylpyridin-4-amine (0.014 g, 0.12 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, DMSO-d6) δ ppm 7.42-7.46 (m, 4H), 7.19-7.33 (m, 16H), 4.31 (s, 1H), 4.15-4.16 (br s, 2H), 3.38-3.47 (m, 4H), 3.35 (t, J=6.3 Hz, 2H), 2.71 (t, J=6.5 Hz, 2H), 2.23-2.29 (m, 4H); MS (DCI+) m/z 530 (M+H)+.

Provenance & Evidence