Benzoic Acid → HCID 13649194, compound

HRID 648982Notes

Reaction equation

HRID 648982 reaction equation
[C:1](O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:25]1([C:31]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][C:37](=[O:42])[CH2:36]3)=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CN(C=O)C>[C:1]([N:28]1[CH2:29][CH2:30][N:25]([C:31]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][C:37](=[O:42])[CH2:36]3)=[O:32])[CH2:26][CH2:27]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 13649191HCID 13649191, compound

Product 1

HCID 13649194HCID 13649194, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 3.2 g of benzoic acid and 4 ml of triethylamine in 50 ml of DMF was added dropwise a solution of 3.87 g of isobutyl chloroformate in 2 ml of DMF. After stirring the mixture for 30 minutes at room temperature, a solution of 8.8 g of 5-(1-piperazinylcarbonyl)oxindol in 3 ml of DMF was added dropwise thereto, and the mixture was stirred for 30 minutes at room temperature and then for 1 hour at 50° to 60° C. The reaction mixture was poured into a large amount of a saturated saline solution, extracted with chloroform, washed with water and dried. The solvent was distilled off, and the residue was recrystallized from methanol to give 1.9 g of 5-(4-benzoyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. waitfor 1 hour at 50° to 60° C
  3. additionThe reaction mixture was poured into a large amount of a saturated saline solution
  4. extractionextracted with chloroform
  5. washwashed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-731167a39b3140b29862f14d067d5ae8
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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