Formaldehyde → HCID 45275162, compound

Participants

Reaction Steps

To a solution of 1-(2-{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl}-2-oxoethyl)-3-phenylpiperazin-2-one (Example 103B, 0.1 g, 0.2 mmol) in methanol was added 30% aqueous formaldehyde solution (0.06 mL, 0.3 mmol) and sodium cyanoborohydride (0.02 g, 0.3 mmol). A few drops of acetic acid were added, and the reaction was stirred at ambient temperature overnight. The reaction mixture was diluted with methylene chloride and washed with aqueous bicarbonate solution. The organic layer was separated, dried over MgSO4, evaporated and chromatographed, eluting with 5% methanol/methylene chloride to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.37-7.42 (m, 2H), 7.26-7.35 (m, 7H), 6.94-7.01 (m, 4H), 4.22 (d, J=15.3 Hz, 1H), 4.21 (s, 1H), 4.09 (d, J=15.5 Hz, 1H), 3.79 (s, 1H), 3.73-3.83 (m, 1H), 3.60 (t, J=4.7 Hz, 2H), 3.34-3.43 (m, 3H), 3.03 (ddd, J=12.0, 4.2, 2.9 Hz, 1H), 2.78 (ddd, J=12.0, 10.7, 3.9 Hz, 1H), 2.29-2.37 (m, 4H), 2.20 (s, 3H); MS (ESI+) m/z 519 (M+H)+.

Provenance & Evidence