1-Methylpiperazine → Tert-butyl 2-(2-(methoxymethoxy)-5-((4-methylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:38][CH2:39][O:40][CH3:41])=[C:14]([CH:37]=1)[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16]>CC(C)=O>[CH3:41][O:40][CH2:39][O:38][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:37][C:14]=1[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[O:16]Participants
4
Procedure
Under ice-cooling, 1-methylpiperazine (0.16 mL) was added to an acetone (2.3 mL) suspension of tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate (0.15 g), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and a 1.0 mol/L aqueous solution of sodium hydroxide and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol] to obtain 0.14 g of tert-butyl 2-(2-(methoxymethoxy)-5-((4-methylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate as a yellow oil substance.