Morpholine → 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one

Participants

Reaction Steps

To a suspension of 10 g (60.8 mmol) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid in 60 mL of dichloromethane was added 11.6 gm (71.8 mmol) of 1,1′-carbonyldiimidazole followed by 5.5 mL (60.8 mmol) of morpholine and 10 mL (60.8 mmol) of N,N-diisopropylethylamine. The dark red reaction mixture was stirred at room temperature overnight and poured into ice water. The organic layer was washed with brine until its pH was 6, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified on a silica gel column eluting with dichloromethane-methanol (98:2) to give 13.84 g (96% yield) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one.

Provenance & Evidence