Potassium Iodide → N-benzyl-N-methyl-1-(1-(4-nitrobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) was added to a suspension of sodium hydride (7.99 mg, 0.200 mmol) in DMF (Volume: 2 ml). The reaction was allowed to stir for 10 minutes at 60° C. 1-(chloromethyl)-4-nitrobenzene (45.7 mg, 0.266 mmol) and potassium iodide (44.2 mg, 0.266 mmol) were added and the reaction was stirred overnight at 60° C. The reaction was diluted with water and ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. It was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 40-100% ethyl acetate:hexanes to afford the product as a white solid. (Yield: 11 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.20-8.12, 7.70-7.62, 7.55, 7.43-7.08, 6.81-6.75, 5.71-5.61, 4.62, 4.56-3.95, 3.21-2.85, 2.74, 1.81-1.13

Provenance & Evidence