Benzoic Acid → HCID 13649194, compound

HRID 648984Notes

Reaction equation

HRID 648984 reaction equation
O1CCOCC1.[C:7](O)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[N:17]1([C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][C:29](=[O:34])[CH2:28]3)=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(Cl)Cl>[C:7]([N:20]1[CH2:21][CH2:22][N:17]([C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][C:29](=[O:34])[CH2:28]3)=[O:24])[CH2:18][CH2:19]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 312751,4-DioxaneHCID 13649192HCID 13649192, compound

Product 1

HCID 13649194HCID 13649194, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixed solvent of 20 ml of dioxane and 20 ml of methylene chloride were added 1.2 g of benzoic acid and 3.0 g of 5-(1-piperazinylcarbonyl)oxindol hydrochloride. To this mixture, a solution of 2.1 g of N,N-dicyclohexylcarbodiimide dissolved in 5 ml of methylene chloride was added dropwise at 10° to 20° C. under ice-cooling externally with stirring. Then, the mixture was stirred for 3.5 hours at the same temperature. Crystals which precipitated were filtered off, and the filtrate was concentrated to dryness under reduced pressure. The resultant residue was dissolved in 100 ml of methylene chloride, and the organic layer was washed, in turn, with 5% aqueous hydrochloric acid solution, 5% aqueous sodium hydrogen carbonate solution, and water, and dried over anhydrous sodium sulfate. Under reduced pressure, the solvent was distilled off and the residue was recrystallized from methanol to give 0.79 g of 5-(4-benzoyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. additionwas added dropwise at 10° to 20° C. under ice-
  2. temperaturecooling externally
  3. stirringThen, the mixture was stirred for 3.5 hours at the same temperature
  4. customCrystals which precipitated
  5. filtrationwere filtered off
  6. concentrationthe filtrate was concentrated to dryness under reduced pressure
  7. dissolutionThe resultant residue was dissolved in 100 ml of methylene chloride
  8. washthe organic layer was washed, in turn, with 5% aqueous hydrochloric acid solution, 5% aqueous sodium hydrogen carbonate solution, and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationUnder reduced pressure, the solvent was distilled off
  11. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-4990532e0d714c498fa64974c8ae233b
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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