1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-{2-[4-(5-Chloropyridin-2-yl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Participants

Reaction Steps

A solution of 1-(5-chloropyridin-2-yl)piperazine (0.037 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 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 25 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.12 (dd, J=2.6, 0.7 Hz, 1H), 7.45 (dd, J=9.0, 2.7 Hz, 1H), 7.18-7.38 (m, 10H), 6.54 (dd, J=9.1, 0.7 Hz, 1H), 4.24 (s, 2H), 3.67-3.72 (m, 2H), 3.54 (t, J=6.6 Hz, 2H), 3.51-3.56 (m, 2H), 3.44-3.50 (m, 2H), 3.36-3.42 (m, 2H), 2.82 (t, J=6.6 Hz, 2H); MS (ESI+) m/z 475 (M+H)+.

Provenance & Evidence