N-Methylbenzylamine → N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Participants

Reaction Steps

1-(1H-indole-2-carbonyl)piperidine-4-carboxylic acid (1.00 g, 3.67 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.408 g, 7.34 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol hydrate (1.125 g, 7.34 mmol) were dissolved in DCM (Volume: 10 ml). The reaction was allowed to stir for 10 minutes before adding DIEA (1.283 ml, 7.34 mmol) and N-methyl-1-phenylmethanamine (0.836 ml, 7.34 mmol). The reaction was allowed to stir overnight at room temperature. The reaction was diluted with water and ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, 1N HCl, and saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using 30% to 60% ethyl acetate:hexanes to obtain product. (Yield: 1.03 g, white solid) 11.53, 7.59-7.54, 7.41-7.11, 7.01, 6.76-6.70, 4.66, 4.52-4.35, 3.22-2.93, 2.76, 1.84-1.51

Provenance & Evidence