Potassium Carbonate → HCID 20480575, compound

HRID 1649227Notes

Reaction equation

HRID 1649227 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.C(=O)([O-])[O-].[K+].[K+].CN(C)P(=O)(N(C)C)N(C)C.[OH:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Cl)=[CH:38][CH:37]=1>O>[OH:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]4)[CH2:2][CH2:3]2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 356844-(Chloromethyl)-phenolHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 20480575HCID 20480575, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1.2 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium carbonate and 20 ml of hexamethylphosphoric triamide was added 651 mg of 4-hydroxybenzyl chloride and the mixture was stirred at 90° C. for 2.5 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. Chloroform was distilled off and the residue was purified through silica gel column chromatography to give 0.3 g of 6-[4-(4-hydroxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril.

Workup

  1. extractionextracted with chloroform
  2. washAfter washing with water
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. distillationChloroform was distilled off
  5. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-31ec1cac1d5049d699d2348ff96c668b
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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