Ethyl bromoacetate → HCID 19357186, compound

HRID 377934Notes

Reaction equation

HRID 377934 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:14][CH2:13]2)=[O:11])=[C:4]([O:28][CH3:29])[CH:3]=1.[H-].[Na+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C)C=O>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:10]([N:9]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:5]3[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=3[O:28][CH3:29])=[O:11])[CH2:13][CH2:14]2)[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 19357045HCID 19357045, compound

Product 1

HCID 19357186HCID 19357186, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(4,5-Dimethyl-2-methoxyphenyl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(0.2 g, 0.5 mmol) was dissolved in dimethylformamide(15 ml), sodium hydride(18.5 mg, 0.5 mmol) was added thereto, and the resulting mixture was stirred at room temperature. Then, ethyl bromoacetate(83.5 mg, 0.5 mmol) was added thereto and the resulting mixture was stirred for 3 hours, concentrated under the reduced pressure to remove the used solvent and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. stirringthe resulting mixture was stirred for 3 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the used solvent
  4. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-fa00cb69fa364ccfb150246ddb08f584
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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