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

Participants

Reaction Steps

To a solution of 1-benzhydrylpiperazine (0.227 g, 0.90 mmol) in dichloromethane (15 mL) under nitrogen was added the product of Example 90D (0.31 g, 0.90 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.344 g, 1.80 mmol) and N,N-dimethylpyridin-4-amine (0.011 g, 0.09 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 7.38-7.42 (m, 4H), 7.15-7.32 (m, 10H), 6.93-7.00 (m, 4H), 4.23 (s, 1H), 4.16 (s, 2H), 3.62-3.66 (m, 2H), 3.47 (t, J=6.4 Hz, 2H), 3.40-3.45 (m, 2H), 2.55-2.65 (m, 2H), 2.36-2.43 (m, 4H), 1.77-1.86 (m, 2H); MS (DCI+) m/z 580 (M+H)+.

Provenance & Evidence