Acetic Acid → HCID 66571572, compound

Participants

Reaction Steps

1-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde (52 mg, 0.143 mmol) was dissolved in EtOH (5 mL) and morpholine (0.025 mL, 0.285 mmol), sodium cyanoborohydride (18 mg, 0.285 mmol), and a catalytic drop of glacial acetic acid were added. Stirring was permitted for 13 h, at which time the solvent was removed in vacuo, the residue was taken up in EtOAc. The organic phase was washed with 10% aq. sodium carbonate, dried over magnesium sulfate, and concentrated. Purification was accomplished via silica gel flash chromatography (30 g silica gel, 100% EtOAc.) The title compound was obtained as an oil. (Yield: 15 mg, 0.034 mmol, 24%) 1H NMR (400 MHz, CDCl3) 7.63, 7.37, 7.27-7.24, 7.14, 7.11-7.04, 6.91, 6.59, 5.47, 4.62, 4.09, 3.67, 2.74, 2.36, 2.08, 1.63, 0.96, 0.61

Provenance & Evidence