Dimethylformamide → HCID 69648868, compound

HRID 1744511Notes

Reaction equation

HRID 1744511 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[C:11]#[N:12])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CN(C)C=O>O>[N+:17]([C:14]1[CH:15]=[CH:16][C:9]([N:4]2[CH2:3][C@@H:2]([CH3:1])[N:7]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@@H:6]([CH3:8])[CH2:5]2)=[C:10]([C:11]#[N:12])[CH:13]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 69648825HCID 69648825, compound

Product 1

HCID 69648868HCID 69648868, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Then, cis-2-(3,5-dimethylpiperazin-1-yl)-5-nitrobenzonitrile (14.3 g), potassium carbonate (4.9 g) and ethyl bromoacetate (6 g) were added to dimethylformamide (35 ml), and the mixture was stirred at 60° C. for 1 h. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform) to give ethyl cis-4-(4-nitro-2-cyanophenyl)-2,6-dimethylpiperazin-1-ylacetate (10.8 g) as an oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform)

Sources & evidence

ORD record
ord-72f355778e2d46d4ace9fd7adafd2545
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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