Triethylamine → 4-Bromo-N-(cyclopropylmethyl)benzamide

Participants

Reaction Steps

Cyclopropylmethylamine (1.62 g, 22.8 mmol) and triethylamine (3 ml) were dissolved in THF (40 ml) and 4-bromobenzoylchloride (5 g, 22.8 mmol) added over 5 min at 0° C. The reaction was stirred at room temperature for 16 h, reduced to dryness under vacuum and the residue partitioned between DCM (75 ml) and water (75 ml). The aqueous was extracted with DCM (2×50 ml). The combined organic phases were washed with brine, dried (magnesium sulphate) and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica eluting with cyclohexane/ethyl acetate (8:2). The solvent was evaporated from the product fractions under vacuum to give 4-bromo-N-cyclopropylmethylbenzamide (4.3 g, 74%). LCMS: retention time 3.00 min, MH+255.

Provenance & Evidence