1-Acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione → 3-[3-Methoxy-4-(trifluoromethyl)benzyl]piperazine-2,5-dione
Reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([O:22][CH3:23])[CH:13]=2)[C:5]1=[O:24])(=O)C>O1CCCC1.[C].[Pd]>[CH3:23][O:22][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[C:18]([F:21])([F:20])[F:19])[CH2:11][CH:6]1[NH:7][C:8](=[O:10])[CH2:9][NH:4][C:5]1=[O:24]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione (1.8 g) in tetrahydrofuran (50 ml) was hydrogenated over 10% palladium-carbon (50% wet, 180 mg) for 5 hours at atmospheric pressure. After removal of the catalyst by filtration, the filtrate was added hydrazine monohydrate (395 mg). The mixture was stirred for 1.5 hours at room temperature and concentrated under reduced pressure. The residue was triturated with isopropyl ether (12 ml) and the precipitates were collected by filtration, and washed with isopropyl ether to give 3-[3-methoxy-4-(trifluoromethyl)benzyl]piperazine-2,5-dione (1.29 g) as a powder.
Workup
- customAfter removal of the catalyst
- filtrationby filtration
- additionthe filtrate was added hydrazine monohydrate (395 mg)
- concentrationconcentrated under reduced pressure
- customThe residue was triturated with isopropyl ether (12 ml)
- filtrationthe precipitates were collected by filtration
- washwashed with isopropyl ether
Sources & evidence
- ORD record
- ord-c44734d33fe84fa8bf2463391e174e10
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166598B2
Reaction notes
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