Water → HCID 18423141, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[C:33](Cl)(=[O:35])[CH3:34]>[Cl-].[Na+].O.C(OCC)(=O)C>[C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1)(=[O:35])[CH3:34]Participants
Procedure
To a-solution of N-(4-((4-(4-aminophenyl)piperazin-1-yl)methyl)phenylmethyl)acetamide (1.8 g) and potassium carbonate (3.1 g) in a mixed solvent of water (50 ml) and ethyl acetate (50 ml) was added dropwise acetyl chloride (0.43 ml) at room temperature over 10 min. This reaction mixture was stirred at room temperature for 4 hr and poured into saturated brine, which was followed by extraction with chloroform. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated to give a purple solid (5.0 g). The obtained solid was subjected to column chromatography (elution solvent; chloroform:methanol=9:1) to give a pale-brown solid. The solid was recrystallized from methanol-water to give the title compound (0.75 g) as pale-red crystals, m.p.=225-226° C.
Workup
- extractionwas followed by extraction with chloroform
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-a42b565241964310a2b42eb0ea719669
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455528B1
Reaction notes
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