Dimethylformamide → HCID 13236322, compound

HRID 1649233Notes

Reaction equation

HRID 1649233 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[CH:30]=[CH2:31]>O>[CH2:31]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:2][CH2:3]1)[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13236322HCID 13236322, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 15 ml of DMF and 1.82 g of potassium carbonate was added 500 mg of allyl bromide and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Then, chloroform was distilled off and the residue was purified through silica gel column chromatography and recrystallized from chloroform-ether to give 0.43 g of 6-(4-allyl-1-piperazinyl)-3,4-dihydrocarbostyril, m.p. 175°-176° C., colorless scales.

Workup

  1. extractionextracted with chloroform
  2. washAfter washing with water
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. distillationThen, chloroform was distilled off
  5. customthe residue was purified through silica gel column chromatography
  6. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-4bba741f731448ddb612f0b15eb1c1b4
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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