Diisopropylethylamine → 1-(2-Oxo-2-{4-[3-(trifluoromethyl)benzyl]piperazin-1-yl}ethyl)-3-phenylpiperidin-2-one

Participants

Reaction Steps

To 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (Example 91D, 0.057 g, 0.244 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.098 g, 0.257 mmol) and 1-(3-(trifluoromethyl)benzyl)piperazine (0.066 g, 0.269 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.064 mL, 0.367 mmol) and the reaction was allowed to stir at room temperature. After stirring overnight, the reaction was loaded directly onto a silica gel column (Analogix®, SF15-12), and the product was eluted using a gradient of 0.4% to 3.75% methanol/dichloromethane over 25 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.58-7.60 (br s, 1H), 7.49-7.55 (m, 2H), 7.41-7.47 (m, 1H), 7.27-7.35 (m, 3H), 7.18-7.26 (m, 2H), 4.47 (d, J=15.7 Hz, 1H), 4.03 (d, J=15.7 Hz, 1H), 3.68-3.73 (m, 1H), 3.59-3.67 (m, 2H), 3.56-3.62 (m, 1H), 3.53-3.59 (m, 2H), 3.47-3.52 (m, 2H), 3.39-3.45 (m, 1H), 2.42-2.49 (m, 4H), 2.17-2.28 (m, 1H), 1.87-2.05 (m, 3H); MS (ESI−) m/z 458 (M−H)−.

Provenance & Evidence