1-(3-(Trifluoromethyl)benzyl)piperazine → 1-(2-Oxo-2-{4-[3-(trifluoromethyl)benzyl]piperazin-1-yl}ethyl)-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

A solution of 1-(3-(trifluoromethyl)benzyl)piperazine (0.395 g, 1.616 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.500 g, 1.616 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.403 g, 2.101 mmol) in dichloromethane (2 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF25-40 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 35 minutes (flow=35 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.40-7.61 (m, 4H), 7.27-7.34 (m, 8H), 7.18-7.25 (m, 2H), 4.23 (s, 2H), 3.64-3.69 (m, 2H), 3.55 (s, 2H), 3.50 (t, J=6.5 Hz, 2H), 3.43-3.49 (m, 2H), 2.60-2.67 (m, 2H), 2.38-2.49 (m, 4H), 1.79-1.89 (m, 2H); MS (ESI+) m/z 536 (M+H)+.

Provenance & Evidence