Dimethylformamide → 4-[2-(1-Pyrrolidinyl)ethoxy]benzamide

Participants

Reaction Steps

To a suspension of 4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid hydrochloride (750 mg, 2.76 mmol) in dry dichloromethane (10 mL) was added oxalyl chloride (0.481 mL, 5.62 mmol, 2.0 eq.) then a catalytic amount of DMF. After 1 h, the reaction mixture was filtered through a pad of diatomaceous earth, then the solvent was removed under reduced pressure. The residue was treated with excess concentrated ammonium hydroxide in THF (5 mL each). The layers were separated by the addition of brine (10 mL); then the aqueous layer was extracted with THF (2×20 mL). The combined extracts were concentrated to dryness under reduced pressure to give the desired amide as a white solid (602 mg, 93%) after drying under vacuum at ambient temperature.

Provenance & Evidence