Benzaldehyde → HCID 9819057, compound

HRID 343301Notes

Reaction equation

HRID 343301 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[N:7]([CH3:11])/[C:6](=[CH:12]\[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)/[C:5]1=[O:21])(=O)C.[H-].[Na+].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C(OCC)(=O)C>[CH:24](=[C:9]1/[C:8](=[O:10])[N:7]([CH3:11])/[C:6](=[CH:12]\[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)/[C:5](=[O:21])[NH:4]/1)\[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 6373052HCID 6373052, compound

Product 1

HCID 9819057HCID 9819057, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3Z)-1-Acetyl-3-(4-methoxybenzylidene)-4-methyl-2,5-piperazinedione (10) (200 mg, 0.69 mmol) and sodium hydride (60% dispersion in oil, 28 mg, 0.69 mmol) in dry DMF (10 ml) was stirred at room temperature for 18 h. Benzaldehyde (71 μl, 0.69 mmol) was then added and the reaction mixture stirred at room temperature for 18 h. It was then diluted with ethyl acetate (100 ml) and washed with brine (4×50 ml). The organic phase was separated, dried (MgSO4), and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, dichloromethane containing 1% MeOH) to give 48 mg (21 w) of a yellow solid.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 18 h
  2. washwashed with brine (4×50 ml)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash chromatography (silica, dichloromethane containing 1% MeOH)
  7. customto give 48 mg (21 w) of a yellow solid

Sources & evidence

ORD record
ord-e1a4d2a21aca4d84acc7d8f7c5838d49
Source dataset
uspto-grants-1999_01
Patent number
US05861400

Reaction notes

Loading…