Sodium hydride → HCID 23021583, compound

HRID 501808Notes

Reaction equation

HRID 501808 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][C:6](=[O:10])[C:5]1=[O:11].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>CN(C)C=O>[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[C:6](=[O:10])[C:5]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 30424332,3-Piperazinedione, 1-methyl-

Product 1

HCID 23021583HCID 23021583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.34 g of 60% sodium hydride was added to a solution of 1.00 g of 1-methyl-2,3-piperazinedione in 10 mL of N,N-dimethylformamide, and this mixture was stirred for 10 minutes at 50° C. Then, 0.88 mL of 4-fluorobenzaldehyde was added thereto and the mixture was stirred for 30 minutes at 120° C. The mixture was cooled to room temperature, and the solvent was distilled out thereof under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; chloroform:ethanol=15:1] to yield 0.80 g of 4-(4-methyl-2,3-dioxo-1-piperazinyl)benzaldehyde as white solid.

Workup

  1. stirringthe mixture was stirred for 30 minutes at 120° C
  2. temperatureThe mixture was cooled to room temperature
  3. distillationthe solvent was distilled out thereof under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography [eluent; chloroform:ethanol=15:1]

Sources & evidence

ORD record
ord-87678b1b30334486b9ab92c5bdaf21f5
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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