[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Cl:18]N1C(=O)CCC1=O>CN(C)C=O>[Cl:18][C:10]1[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][C:3]([C:4]([NH:6][CH3:7])=[O:5])=[C:2]([CH3:1])[CH:11]=1100 mg (0.427 mmol) of 2,N-dimethyl-5-morpholin-4-ylbenzamide prepared in Step A was dissolved in 3 ml of N,N-dimethylformamide, and thereafter, 63 mg (0.47 mmol) of N-chlorosuccinimide was added thereto under cooling on ice. The obtained mixture was stirred at 50° C. for 1 hour. Thereafter, the reaction solution was concentrated, and water was then added thereto. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. The extract was concentrated, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate:methylene chloride=1:5), so as to obtain 54.5 mg (47%) of 4-chloro-2,N-dimethyl-5-morpholin-4-ylbenzamide in the form of a colorless solid, as well as 46 mg (40%) of 2-chloro-6,N-dimethyl-3-morpholin-4-ylbenzamide in the form of a colorless solid.
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