1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-4-yl)propyl)piperidine-4-carboxamide

Participants

Reaction Steps

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (0.350 g, 0.882 mmol), 1-hydroxybenzotriazole (0.149 g, 1.103 mmol), and EDC (0.211 g, 1.103 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir at room temperature for 15 minutes before adding Hunig's Base (0.321 mL, 1.838 mmol) and 2-(pyridin-4-yl)propan-1-amine (0.100 g, 0.735 mmol) as a 2 mL DCM solution. The reaction was allowed to stir overnight. The reaction was dissolved in water and ethyl acetate. The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride. It was then dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in ethyl acetate to obtain product. (Yield: 151 mg) 1H-NMR (500 MHz, CDCl3) 8.59-8.51, 7.65, 7.34, 7.22-7.12, 7.06-6.99, 6.62, 5.46, 5.31, 4.69-4.03, 3.64-3.53, 3.36-3.27, 3.06-2.95, 2.89-2.78, 2.23-2.13, 1.87-1.25

Provenance & Evidence