Dimethylamine, hydrochloride → 2,6-dimethoxy-N,N-dimethylbenzamide

Participants

Reaction Steps

A mixture of 2,6-dimethoxybenzoic acid (102 mg, 0.56 mmol), dimethylamine hydrochloride (91 mg, 1.12 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (234 mg, 0.73 mmol) and diisopropylethylamine (390 μL, 2.24 mmol) in DMF (1 mL) was stirred at ambient temperature overnight. The reaction mixture was taken up in ethyl acetate (50 mL) and aqueous. NaHCO3(50 mL). The organic phase was washed with brine (2×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide titled compound (66 mg). MS (APCI(+)) m/e 210 (M+H)+.

Provenance & Evidence