Acetic Acid → HCID 66571626, compound

Participants

Reaction Steps

1-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde (86 mg, 0.236 mmol) was dissolved in EtOH (5 mL) and N-methylbenzylamine (0.027 mL, 0.283 mmol), sodium cyanoborohydride (30 mg, 0.472 mmol), and a catalytic drop of glacial acetic acid were added. Stirring was permitted for 14 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: 23 mg, 0.049 mmol, 20%) 1H NMR (400 MHz, CDCl3) 7.62, 7.37-7.23, 7.14, 7.08-7.02, 6.82, 6.57, 5.45, 4.60, 4.04, 3.44, 2.75, 2.16, 2.10, 1.83-1.59, 0.91, 0.51

Provenance & Evidence