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

HRID 544963Notes

Reaction equation

HRID 544963 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([N:12]1[CH2:17][C:16](=[O:18])[N:15](C(=O)C)[CH2:14][C:13]1=[O:22])(=[O:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:9]([N:12]1[CH2:17][C:16](=[O:18])[NH:15]/[C:14](=[CH:1]\[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)/[C:13]1=[O:22])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10796Cesium carbonateHCID 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

To a solution of benzaldehyde 4 (0.54 g, 5.05. mmol) in DMF (5 mL) was added compound 1 (2.0 g, 10.1 mmol) and the solution was repeatedly evacuated in a short time to remove oxygen and flushed with Ar, followed by the addition of Cs2CO3 (1.65 g, 5.05 mmol) and the evacuation-flushing process was repeated again. The resultant mixture was stirred for 3.5 h at room temperature. After the solvent was removed by evaporation, the residue was dissolved in the mixture of EtOAc and 10% Na2CO3, and the organic phase was washed with 10% Na2CO3 again and saturated NaCl for three times, dried over Na2SO4 and concentrated in vacuo. The residual solid was recrystalized from MeOH-ether to obtain a off-white solid of 17; yield 1.95 g (79%).

Workup

  1. customthe solution was repeatedly evacuated in a short time
  2. customto remove oxygen
  3. customflushed with Ar
  4. customAfter the solvent was removed by evaporation
  5. dissolutionthe residue was dissolved in the mixture of EtOAc and 10% Na2CO3
  6. washthe organic phase was washed with 10% Na2CO3 again
  7. dry with materialsaturated NaCl for three times, dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residual solid was recrystalized from MeOH-ether

Sources & evidence

ORD record
ord-1053d9f411024d2eb9213e673d1d3779
Source dataset
uspto-grants-2011_05
Patent number
US07935704B2

Reaction notes

Loading…