Water → HCID 13649215, compound

HRID 648978Notes

Reaction equation

HRID 648978 reaction equation
[N:1]1([CH2:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[O:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].O.[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32]>CC(C)=O>[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[O:9])[CH2:2][CH2:3]1)=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69252Benzoyl chloride, 3-chloro-HCID 13649213HCID 13649213, compound

Product 1

HCID 13649215HCID 13649215, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a suspension comprising 1.0 g of dihydrochloric acid salt of 5-[2-(1-piperazinyl)acetyl]oxindol, 0.63 gof potassium carbonate, 5 ml of water and 10 ml of acetone was added dropwise a solution of 0.63 g of m-chlorobenzoyl chloride in 2 ml of acetone under ice-cooling with stirring, and the mixture was stirred for 1.5 hours at the same temperature. After completion of reaction, the reaction mixture was poured into ice-water and extracted with chloroform. The chloroform layer was washed, in turn, with water and a saturated saline solution, and dried over sodium sulfate. The solvent was then distilled off under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent: chloroform:methanol=20:1) and recrystallized from a mixture of ethanol and chloroform to give 0.34 g of 5-[2-[4-(3-chlorobenzoyl)-1-piperazinyl]acetyl]oxindol.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours at the same temperature
  3. customAfter completion of reaction
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed, in turn, with water
  6. dry with materiala saturated saline solution, and dried over sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe resultant residue was purified by silica-gel column chromatography (eluent: chloroform:methanol=20:1)
  9. customrecrystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record
ord-4578a748f839440388fc7ad4918504fe
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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