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

Participants

Reaction Steps

A solution of 1-(4-fluorophenyl)piperazine (0.034 g, 0.186 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol) in dichloromethane (2 mL) was stirred at room temperature. After stirring overnight, the reaction mixture 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 75% ethyl acetate/hexanes over 25 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.27-7.38 (m, 8H), 7.18-7.25 (m, 2H), 6.94-7.01 (m, 2H), 6.80-6.85 (m, 2H), 4.24 (s, 2H), 3.73 (t, J=4.9 Hz, 2H), 3.54-3.60 (m, 2H), 3.54 (t, J=6.5 Hz, 2H), 3.02 (t, J=5.0 Hz, 2H), 2.89 (t, J=5.2 Hz, 2H), 2.82 (t, J=6.5 Hz, 2H).

Provenance & Evidence