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

HRID 1584768Notes

Reaction equation

HRID 1584768 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 (described by Marcuccio and Elix in Aust. J. Chem, 1984, 37, 1791) (25.0 g, 126 mmol) was treated at 130° C. in DMF (200 ml) with triethylamine (17.6 ml, 126 mmol) and benzaldehyde (13.0 ml, 126 mmol). After 4 hours the mixture was cooled to room temperature and poured into EtOAc (1000 ml) and washed 3 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 1-acetyl-3-benzylidene-2,5-piperazinedione.

Workup

  1. washwashed 3 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-2ca802fb7d484af5b1e20e07b1bae720
Source dataset
uspto-grants-1999_08
Patent number
US05935955

Reaction notes

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