Triethylamine → (3Z)-1-acetyl-3-(4-acetamidobenzylidene)-2,5-piperazinedione

HRID 442653Notes

Reaction equation

HRID 442653 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:15]([NH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)(=[O:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:11]([N:7]1[CH2:6][C:5](=[O:14])[NH:4]/[C:9](=[CH:23]\[C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[CH:26][CH:25]=2)/[C:8]1=[O:10])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 739424-AcetamidobenzaldehydeHCID 5403711,4-Diacetyl-2,5-piperazinedione

Product 1

HCID 67581664(3Z)-1-acetyl-3-(4-acetamidobenzylidene)-2,5-piperazinedioneYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1,4-Diacetyl-2,5-piperazinedione (10.0 g, 50 mmol), prepared by the published procedure mentioned in Example 3, was stirred in DMF (40 ml) with 4-acetamidobenzaldehyde (8.24 g, 50 mmol) and triethylamine (7 ml, 50 mmol) and heated to 120° C. After 21/2 h the mixture was cooled to room temperature, diluted with EtOAc (100 ml) and stirred overnight. The solid formed was collected, washed with EtOAc and dried to give 8.46 g (56%) of a yellow solid.

Workup

  1. temperatureAfter 21/2 h the mixture was cooled to room temperature
  2. customThe solid formed
  3. customwas collected
  4. washwashed with EtOAc
  5. customdried

Sources & evidence

ORD record
ord-d95d9aa19b2f40f880e0eca605511175
Source dataset
uspto-grants-1999_04
Patent number
US05891877

Reaction notes

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