Hydrochloric Acid → HCID 53656911, compound

HRID 1859169Notes

Reaction equation

HRID 1859169 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]1=[O:13].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].Cl>C(OCC)(=O)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:8](=[O:12])[C:7]1=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 127069801-[(2,4-Dimethoxyphenyl)methyl]piperazine-2,3-dione

Product 1

HCID 53656911HCID 53656911, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 10.0 g of 1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, 1.66 g of sodium hydride (60%, oil) and 100 ml of N,N-dimethylformamide was stirred at 50° C. for 30 minutes and then cooled to room temperature. To the reaction mixture was added 3.6 ml of methyl bromoacetate, after which the resulting mixture was stirred at the same temperature for 30 minutes and added to a mixed solvent of 200 ml of ethyl acetate and 200 ml of ice water, and the pH was adjusted to 2 with 2N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with five 50-ml portions of ethyl acetate. The combined organic layer was washed with 50 ml of water and then a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=10:1) to obtain 10.7 g of methyl [4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazin-1-yl]acetate as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. stirringafter which the resulting mixture was stirred at the same temperature for 30 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with five 50-ml portions of ethyl acetate
  5. washThe combined organic layer was washed with 50 ml of water
  6. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-51758f43d3094d62934d3bba5617af3e
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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