1-(Bis(4-fluorophenyl)methyl)piperazine → 1-(2-{4-[Bis(4-fluorophenyl)methyl]piperazin-1-yl}-2-oxoethyl)-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

To a solution of 1-(bis(4-fluorophenyl)methyl)piperazine (0.14 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 7.18-7.36 (m, 14H), 6.95-7.01 (m, 4H), 4.22 (s, 1H), 4.19 (s, 2H), 3.63 (t, J=4.7 Hz, 2H), 3.48 (t, J=6.4 Hz, 2H), 3.41-3.46 (m, 2H), 2.60-2.65 (m, 2H), 2.31-2.39 (m, 4H), 1.78-1.87 (m, 2H)); MS (DCI+) m/z 580 (M+H)+.

Provenance & Evidence