Sodium Chloride → HCID 3067179, compound

HRID 1462535Notes

Reaction equation

HRID 1462535 reaction equation
[O:1]=[C:2]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]2)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[H-].[Na+].[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].C([O-])(=O)C([O-])=O>CN(C)C=O.CC(C)=O>[CH3:30][N:23]1[C:24]2[C:19](=[CH:18][C:17]([C:2](=[O:1])[CH2:3][CH2:4][N:5]3[CH2:6][CH2:7][N:8]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:9][CH2:10]3)=[CH:26][CH:25]=2)[CH2:20][CH2:21][C:22]1=[O:27]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6101p-Toluenesulfonic acidHCID 24758Sodium hydrideHCID 71081OxalateHCID 30670732(1H)-Quinolinone, 3,4-dihydro-6-(1-oxo-3-(4-phenyl-1-piperazinyl)propyl)-

Product 1

HCID 3067179HCID 3067179, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

1.8 Grams of 6-[1-oxo-3-(4-phenyl-1-piperazinyl)-propyl]-3,4-dihydrocarbostyril and 0.24 g of of sodium hydride (50% in mineral oil) were mixed in 50 ml of dimethylformamide and stirred at a room temperature for 3 hours. Then 0.9 g of p-toluenesulfonic acid was added and stirred at a room temperature for 3 hours. The reaction mixture was poured into 150 ml of a saturated sodium chloride solution and was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation under a reduced pressure. The residue thus obtained was injected into preparative thin-layer chromatography to purify and separate the desired compound. The compound obtained was dissolved in acetone and converted into the oxalate by a method similar to that described in Example 27 and recrystallized from ethanol-water to obtain 1.5 g of 1-methyl-6-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril.monooxalate in colorless flake-like crystals.

Workup

  1. stirringstirred at a room temperature for 3 hours
  2. extractionwas extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation under a reduced pressure
  6. customThe residue thus obtained
  7. customto purify
  8. customseparate the desired compound
  9. customThe compound obtained
  10. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-9d5a33dd611441a2aa25f4e1d1b90647
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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