Dimethylamine → N-dimethylaminoacetyl-N-(3-dimethylamino-4-methoxymethoxybenzyl)aniline
Reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([N:23]([CH3:25])[CH3:24])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:26][NH:27][CH3:28]>>[CH3:26][N:27]([CH2:2][C:3]([N:5]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([N:23]([CH3:25])[CH3:24])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4])[CH3:28]Participants
3
Procedure
To the compound (2) (1.68 g, 4.63 mmol) obtained above was added a 50% aqueous solution of dimethylamine (8 ml) under ice-cooling. After being stirred at room temperature for 1.5 hours, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the object compound (3). Yield 1.57 g (91%).
Workup
- temperaturecooling
- extractionthe reaction mixture was extracted with ethyl acetate