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

HRID 343298Notes

Reaction equation

HRID 343298 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-7c1c9b0b9ef044c3a4b32a53a834ee14
Source dataset
uspto-grants-1999_01
Patent number
US05861400

Reaction notes

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