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

Participants

Reaction Steps

The following was added sequentially to DCM: 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid (600 mg, 1.73 mmol), TEA (0.725 mL, 5.19 mmol), EDC (365 mg, 1.903 mmol), and HOBt (291 mqg, 1.903 mmol). This was allowed to stir at rt for 30 min, at which time pyridylethylamine (0.227 mL, 1.903 mmol) was added. Stirring continued for 18 h. At this time, the DCM and TEA were stripped off, and the residue was taken up in EtOAc and washed with 10% aqueous sodium carbonate (3×). The organic phase was collected, dried over magnesium sulfate, and concentrated in vacuo. The resulting solid/oil mixture was recrystallized from EtOAc to afford the title compound as small, white crystals. (Yield: 586 mg, 1.29 mmol, 75%) 1H NMR (400 MHz, CDCl3) 8.50, 7.21, 7.09, 7.02, 6.78, 6.30, 6.11, 5.55-5.42, 5.25, 4.32, 3.52, 2.87-2.71, 2.28-2.10, 1.72-1.65, 1.42-1.25

Provenance & Evidence