1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-hydroxybenzotriazole (51.1 mg, 0.378 mmol), and EDCI (72.5 mg, 0.378 mmol) were dissolved in 2.0 mL of DCM. The reaction was allowed to stir at room temperature for 10 minutes before 2-(3-methoxyphenyl)ethanamine (0.056 ml, 0.378 mmol) and Hunig's Base (0.066 ml, 0.378 mmol) were added as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The crude material was triturated with ethyl acetate to obtain product as a white solid. (Yield: 89 mg, white solid)
