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

HRID 1075446Notes

Reaction equation

HRID 1075446 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-piperazinedione2×

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), which is compound (8) mentioned in Reference Example 1 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-95f7566b982f41648d5348d3025ea71d
Source dataset
uspto-grants-1999_05
Patent number
US05902812

Reaction notes

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