Sodium Hydroxide → HCID 72188143, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-isopropyl-6-methoxy-4-morpholin-4-yl-benzamide (0.31 g, 1.1 mmol) in tetrahydrofuran/benzene (1:2) (10 ml) is added tetrabutylammonium hydrogen sulfate (38.0 mg, 0.10 mmol) followed by the addition of 30% aqueous sodium hydroxide (10 ml) at room temperature. A solution of 4-chloro-benzyl bromide (0.23 g, 1.1 mmol) in tetrahydrofuran (4 ml) is slowly added to the solution and the resulting mixture is heated to 90° C. for 45 min. The mixture is cooled to room temperature and extracted with ethyl acetate (3×10 ml). The combined organic layers are washed with water (10 ml), brine (10 ml), dried over anhydrous sodium sulfate and concentrated in vacuo to get crude product, which is purified by flash column chromatography (silica gel, 10% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-isopropyl-6-methoxy-4-morpholin-4-yl-benzamide (example 40) (0.115 g, 0.45 mmol, 28%). [M+H]+ 403.2.

Provenance & Evidence