Benzaldehyde → 1-Acetyl-3-benzylidene-2,5-piperazinedione

HRID 1289467Notes

Reaction equation

HRID 1289467 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[N:7]([C:11](=[O:13])[CH3:12])[CH2:6][C:5]1=[O:14])(=O)C.C(N(CC)CC)C.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCOC(C)=O>CN(C=O)C>[C:11]([N:7]1[CH2:6][C:5](=[O:14])[NH:4][C:9](=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]1=[O:10])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5403711,4-Diacetyl-2,5-piperazinedione

Product 1

HCID 37596531-Acetyl-3-benzylidene-2,5-piperazinedioneYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Diacetyl-2,5-piperazinedione (25.0 g, 126 mmol) was heated at 120°-130° C. in DMF (200 ml) with triethylamine (17.6 ml, 126 mmol) and benzaldehyde (13.0 ml, 126 mmol). After 4 h the mixture was cooled to room temperature and poured into EtOAc (1000 ml), and washed three times with brine. Any solid formed at this stage was filtered off. The filtrate was dried (MgSO4) and the solvent removed in vacuo. The residue was recrystallised from EtOAc:Hexane to give 11.78 g (38%) of the title compound as a yellow solid.

Workup

  1. washwashed three times with brine
  2. customAny solid formed at this stage
  3. filtrationwas filtered off
  4. dry with materialThe filtrate was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was recrystallised from EtOAc

Sources & evidence

ORD record
ord-7ad985d0f81a44dd864be3002cf0d55a
Source dataset
uspto-grants-1998_05
Patent number
US05750530

Reaction notes

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