Benzaldehyde → (Z)-1-Acetyl-3-benzylidenepiperazine-2,5-dione

HRID 442652Notes

Reaction equation

HRID 442652 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 5915153(Z)-1-Acetyl-3-benzylidenepiperazine-2,5-dione

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 3, 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.

Workup

  1. washwashed three times with brine
  2. customAny solid formed at this stage
  3. filtrationwas filtered off

Sources & evidence

ORD record
ord-62547bda284249ac8cb248340172cbed
Source dataset
uspto-grants-1999_04
Patent number
US05891877

Reaction notes

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