Diisopropylethylamine → Morpholine-4-carboxylic acid (4-bromo-2-dimethylcarbamoyl-phenyl)-amide

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-bromo-N,N-dimethyl-benzamide (2.00 g, 8.22 mmol), di-iso-propyl ethyl amine (6.5 ml, 37.32 mmol), 4-morpholinecarbonyl chloride (4.3 ml, 37.46 mmol), and chloroform (20 ml) were combined and stirred for 18 hours at 50° C. The organic layer was washed with water, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (50% to 100% ethyl acetate in hexanes) to give 1.13 g (39%) of morpholine-4-carboxylic acid (4-bromo-2-dimethylcarbamoyl-phenyl)-amide. 1H-NMR (250 MHz, DMSO-d6) δ 8.67 (s, 1H), 7.56-7.45 (m, 2H), 7.42 (t, J=9.3 Hz, 4H), 3.35-3.28 (m, 4H), 2.96-2.86 (m, 6H); MS: m/z 356.0+358.1 (M+H+).

Provenance & Evidence