Dimethylformamide → N-(4-acetyl-1-piperazinyl)-N-benzyl-4-fluorobenzamide
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CN(C)C=O.[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of N-(4-acetyl-1-piperazinyl)-4-fluorobenzamide (230 mg) and N,N-dimethylformamide (3 ml) was added sodium hydride (60% oil dispersion, 35 mg) in one portion at 0° C. The mixture was stirred at 0° C. for 1 hour then benzyl bromide (0.17 ml) was added to this mixture at 0° C. After stirring at 0° C. for 1.5 hours, water was added and the solvent was evaporated. The residue was taken up in ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and ethyl acetate (1:5) to give crystals. Crystallization from ethyl acetate and n-hexane to give N-(4-acetyl-1-piperazinyl)-N-benzyl-4-fluorobenzamide (260 mg).
Workup
- stirringAfter stirring at 0° C. for 1.5 hours
- customthe solvent was evaporated
- washwashed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography
- washeluting with a mixture of methanol and ethyl acetate (1:5)
- customto give crystals
- customCrystallization from ethyl acetate and n-hexane
Sources & evidence
- ORD record
- ord-774f2a7ce9534c7dbaad8de8ca3bab03
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291464B1
Reaction notes
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