1-(3-(Trifluoromethyl)benzyl)piperazine → 3,3-Bis(4-fluorophenyl)-1-(2-oxo-2-{4-[3-(trifluoromethyl)benzyl]piperazin-1-yl}ethyl)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of 1-(3-(trifluoromethyl)benzyl)piperazine (0.24 g, 1.00 mmol) in dichloromethane (25 mL) under nitrogen was added 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (Example 58D, 0.33 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.39 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 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). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.59 (m, 4H), 7.27-7.35 (m, 4H), 6.96-7.03 (m, 4H), 4.18 (s, 2H), 3.59-3.63 (m, 2H), 3.53 (s, 2H), 3.51 (t, J=6.6 Hz, 2H), 3.41-3.45 (m, 2H), 2.77 (t, J=6.5 Hz, 2H), 2.40-2.44 (m, 2H), 2.31-2.35 (m, 2H); MS (DCI+) m/z 558 (M+H)+.

Provenance & Evidence