Sodium Hydroxide → HCID 72187943, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)-benzoic acid ethyl ester (0.27 g, 0.85 mmol), 4-chlorobenzylamine (1.21 g, 8.51 mmol) and trimethylaluminium (2M in toluene) (2.98 ml, 5.96 mmol) in toluene (9 ml) is heated at 110° C. for 4 d. After completion of the reaction (monitored by TLC), a 2M aqueous solution of sodium hydroxide is carefully added and the mixture is extracted with ethyl acetate (2×15 ml). The combined organic layers are washed with 2M aqueous solution of sodium hydroxide (10 ml), brine (10 ml) and dried over sodium sulfate. The solvent is evaporated to get the crude product, which is purified by column chromatography (silica gel, 30% ethyl acetate/cyclohexane) to afford N-[(4-chlorophenyl)-methyl]-2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)-benzamide (example 19) (0.28 g, 0.68 mmol, 80%). [M+H]+ 413.1.

Provenance & Evidence