Dicyclohexylcarbodiimide → HCID 13649190, compound

HRID 648979Notes

Reaction equation

HRID 648979 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:29]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1>[CH2:29]([N:36]1[CH2:41][CH2:40][N:39]([C:1]([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7]3)=[O:3])[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 759941-BenzylpiperazineHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 13649190HCID 13649190, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Carboxyoxindol (0.93 g), 1.3 g of DCC, and 1.1 g of benzylpiperazine were suspended in 10 ml of dioxane, and the suspension was stirred at 60° to 70° C. for 5 hours. After completion of reaction, the solvent was distilled off and ethyl ether was added to the residue and crystals which precipitated were filtered off. After concentrating the filtrate, the residue was dissolved with an addition of chloroform. The solution was washed with water and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was distilled off. The residue were recrystallized from isopropyl alcohol to give 300 mg of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. customAfter completion of reaction
  2. distillationthe solvent was distilled off
  3. additionethyl ether was added to the residue and crystals which
  4. customprecipitated
  5. filtrationwere filtered off
  6. concentrationAfter concentrating the filtrate
  7. dissolutionthe residue was dissolved with an addition of chloroform
  8. washThe solution was washed with water
  9. dry with materialAfter drying over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue were recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-16ec085105a242e1a2a8f094caab520f
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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