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

Participants

Reaction Steps

A solution of 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (Example 91D, 0.050 g, 0.214 mmol), 1-(bis(4-fluorophenyl)methyl)piperazine (0.068 g, 0.236 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.062 g, 0.322 mmol) in dichloromethane (0.5 mL) was allowed to stir at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 15 minutes, maintaining 100% ethyl acetate for an additional 10 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.38 (m, 9H), 6.93-7.04 (m, 4H), 4.42 (d, J=15.5 Hz, 1H), 4.23 (s, 1H), 4.00 (d, J=15.5 Hz, 1H), 3.70 (dd, J=5.8, 4.6 Hz, 1H), 3.59-3.66 (m, 2H), 3.52-3.60 (m, 1H), 3.44-3.50 (m, 2H), 3.37-3.46 (m, 1H), 2.33-2.41 (m, 4H), 2.15-2.27 (m, 1H), 1.92-2.05 (m, 2H), 1.78-1.91 (m, 1H); MS (ESI−) m/z 502 (M−H)−.

Provenance & Evidence