1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2,3-dihydro-1H-inden-2-yl)piperidine-4-carboxamide

Participants

Reaction Steps

The following was added sequentially to DCM (2 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), DIPEA (0.07 mL, 0.378 mmol), EDC (30 mg, 0.151 mmol), HOBT (24 mg, 0.151 mmol), and 2-aminoindane (0.020 mL, 0.151 mmol). The mixture was stirred for 36 h at rt, at which time the solution diluted with a 1:1 solution of ethyl acetate:diethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×), which resulted in a precipitate that failed to go into either phase. The precipitate was collected and washed with water and diethyl ether to afford the title compound as a white solid. (Yield: 52 mg, 0.102 mmol, 81%) 1H NMR (400 MHz, CDCl3) 7.64, 7.33-7.14, 7.03, 6.64, 5.62, 5.51, 4.76, 4.4, 3.33, 2.84-2.75, 2.21, 1.75

Provenance & Evidence