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)piperidine (0.030 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 column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 70% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.46-7.09 (m, 12H), 7.03 (m, 2H), 4.58-4.23 (m, 2H), 3.57 (m, 2H), 2.72-2.55 (m, 2H), 2.45-2.23 (m, 2H), 2.02-1.75 (m, 3H), 1.75-1.47 (m, 6H); MS (DCI+) m/z 471 (M+H)+.
