1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-{2-[2-(4-Fluorophenyl)pyrrolidin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

A solution 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 68E, 0.050 g, 0.169 mmol) and 2-(4-fluorophenyl)pyrrolidine (0.028 g, 0.169 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF10-4 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 7.42-6.83 (m, 14H), 5.14 (m, 1H), 4.64-4.10 (m, 1H), 3.97-3.73 (m, 2H), 3.73-3.47 (m, 2H), 3.25-2.91 (m, 1H), 2.78-2.15 (m, 3H), 1.85 (m, 5H)); MS (DCI+) m/z 457 (M+H)+.

Provenance & Evidence