Benzylamine → N-benzyl-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

Participants

Reaction Steps

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (200 mg, 0.500 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (115 mg, 0.600 mmol), and 1-Hydroxybenzotriazole (81 mg, 0.600 mmol) were dissolved in 10.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (131 μL, 0.750 mmol) and benzylamine (82 μL, 0.750 mmol) were added. The reaction was allowed to stir overnight. The reaction was diluted with water and dichloromethane. The layers were separated and the organic layer was washed with water, saturated ammonium chloride, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 10 gram silica Biotage column, with the gradient 30% ethyl acetate: hexanes to 100% ethyl acetate. After purification, pure white solid was obtained. Yield: 105 mg (White solid)

Provenance & Evidence