N,O-Dimethylhydroxylamine → 4-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide

Participants

Reaction Steps

EDCI (4.44 g, 23.18 mmol) was added portionwise to a solution of 4-hydroxy-3-(morpholinomethyl)benzoic acid (5 g, 21.07 mmol), N,O-dimethylhydroxylamine (2.67 g, 27.40 mmol), DIPEA (4.05 mL, 23.18 mmol) and HOBt (3.55 g, 23.18 mmol) in DMF (25 mL) whilst maintaining the temperature below 10° C. The mixture was stirred for 48 h, diluted with EtOAc (200 mL), washed with saturated NaHCO3 (200 mL), water (2×100 mL) & brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography on silica with EtOAc as eluent to give the sub-title compound as a colourless oil. Yield: 3.20 g

Provenance & Evidence