Sodium Chloride → 1-Benzyl-6-{3-[4-(3-methylphenyl)-1-piperazinyl]-2-propenyl}-3,4-dihydrocarbostyril monooxalate

HRID 2291200Notes

Reaction equation

HRID 2291200 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]=[CH:15][CH2:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[Na+].CC(C)=O.[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46]>CC(C)=O.CN(C)C=O>[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46].[CH2:30]([N:23]1[C:24]2[C:19](=[CH:18][C:17]([CH2:16][CH:15]=[CH:14][N:11]3[CH2:12][CH2:13][N:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=4)[CH2:9][CH2:10]3)=[CH:26][CH:25]=2)[CH2:20][CH2:21][C:22]1=[O:27])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 542376266-{3-[4-(3-Methylphenyl)-1-piperazinyl]-2-propenyl}-3,4-dihydrocarbostyrilHCID 88629647Oxalic acid acetone

Product 1

HCID 1317145131-Benzyl-6-{3-[4-(3-methylphenyl)-1-piperazinyl]-2-propenyl}-3,4-dihydrocarbostyril monooxalate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

1.8 Grams of 6-{3-[4-(3-methylphenyl)-1-piperazinyl]-2-propenyl}-3,4-dihydrocarbostyril and 0.25 g of sodium hydride (50% in mineral oil) were mixed into 60 ml of dimethylformamide and the mixture was stirred at a room temperature for 2 hours then 0.7 g of benzyl chloride was added to the reaction mixture and stirred at a room temperature for 8 hours. The reaction mixture was poured into 150 ml of saturated sodium chloride aqueous solution and was extracted with chloroform, the chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was purified by a silica-gel column chromatography and an oily substance thus obtained was dissolved in 20 ml of acetone, then under stirring condition, the pH of the solution was adjusted to pH 3 to 4 by adding 5%-oxalic acid acetone solution to obtain precipitates. The precipitates were collected by filtration and washed with acetone then recrystallized from ethanol to obtain 2.2 g of 1-benzyl-6-{3-[4-(3-methylphenyl)-1-piperazinyl]-2-propenyl}-3,4-dihydrocarbostyril monooxalate in colorless needle-like crystals, having the melting point of 176°-178° C.

Workup

  1. stirringstirred at a room temperature for 8 hours
  2. extractionwas extracted with chloroform
  3. washthe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation
  6. customThe residue thus obtained
  7. customwas purified by a silica-gel column chromatography
  8. customan oily substance thus obtained
  9. stirringunder stirring condition
  10. customto obtain
  11. customprecipitates
  12. filtrationThe precipitates were collected by filtration
  13. washwashed with acetone
  14. customthen recrystallized from ethanol

Sources & evidence

ORD record
ord-15266df8a3464965a9ef7181ba920bd4
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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