Morpholine → (1H-Indol-6-yl)(morpholino)methanone

Participants

Reaction Steps

A solution of morpholine (1.320 mL, 15.14 mmol), 1H-indole-6-carboxylic acid (2.0332 g, 12.62 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (3.63 g, 18.92 mmol), 1-hydroxybenzotriazole (HOBt) (2.90 g, 18.92 mmol) and diisopropylethylamine (DIPEA) (6.61 mL, 37.8 mmol) in DMF (31.5 mL) was stirred overnight. The reaction was poured into a 1:1 water:brine solution and extracted with EtOAc (2×). The organic layers were combined and washed with 0.25 M aqueous KHSO4, water, brine and 10% aqueous LiCl; dried over Na2SO4, filtered and concentrated in vacuo. Trituration with Et2O provided the desired product (2.20 g, 9.58 mmol, 76% yield) as a light tan solid.

Provenance & Evidence