Water → 1-Acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione

HRID 1375019Notes

Reaction equation

HRID 1375019 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[CH:6]=O.[C:15]([N:18]1[CH2:23][C:22](=[O:24])[N:21](C(=O)C)[CH2:20][C:19]1=[O:28])(=[O:17])[CH3:16].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(C)(C)C.C(OCC)(=O)C>[C:15]([N:18]1[CH2:23][C:22](=[O:24])[NH:21][C:20](=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:19]1=[O:28])(=[O:17])[CH3:16]

Participants

8

Reactant 4

HCID 962WaterHCID 5403711,4-Diacetyl-2,5-piperazinedioneHCID 179641703-Methoxy-4-(trifluoromethyl)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 694200991-Acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of crude 3-methoxy-4-(trifluoromethyl)-benzaldehyde and 1,4-diacetylpiperazine-2,5-dione (1.98 g) in a mixture of N,N-dimethylformamide (10 ml) and tert-butanol (10 ml) was added potassium tert-butoxide (1.12 g) at 5° C. The mixture was stirred for 18 hours at room temperature. Water (30 ml) and ethyl acetate (100 ml) were added to the mixture and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with 50% of ethyl acetate in hexane as an eluent to give 1-acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione (2.11 g) as a powder.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with 50% of ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-f49e23d9496549a4970675962c087491
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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