1-(2,4-Dichlorobenzyl)piperazine → 1-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Participants

Reaction Steps

A mixture of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and 1-(2,4-dichlorobenzyl)piperazine (0.046 g, 0.186 mmol) in dichloromethane (0.5 mL) was stirred 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 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.20-7.39 (m, 13H), 4.19 (s, 2H), 3.59 (t, J=4.8 Hz, 2H), 3.53 (s, 2H), 3.52 (t, J=6.4 Hz, 2H), 3.42 (t, J=4.9 Hz, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.43 (t, J=4.9 Hz, 2H), 2.32 (t, J=4.9 Hz, 2H); MS (ESI+) m/z 522 (M+H)+.

Provenance & Evidence