Diisopropylethylamine → 1-(2-{4-[Bis(4-fluorophenyl)methylene]piperidin-1-yl}-2-oxoethyl)-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

To a solution of 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E) (0.144 g, 0.47 mmol) and 4-(bis(4-fluorophenyl)methylene)piperidine hydrochloride (European Journal of Medicinal Chemistry; 22, 1987; 243-250) (0.15 g, 0.47 mmol) in methylene chloride (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.177 g, 0.47 mmol) and diisopropylethylamine (0.4 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with methylene chloride, and washed with 1 N HCl, water, 1 N NaOH, and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography, eluting with 5% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.17-7.33 (m, 10H), 6.96-7.05 (m, 8H), 4.24 (s, 2H), 3.66 (t, J=5.5 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 3.42-3.48 (m, 2H), 2.62-2.67 (m, 2H), 2.29-2.42 (m, 4H), 1.75-1.89 (m, 2H); MS (ESI+) m/z 577 (M+H)+.

Provenance & Evidence