Veratric Acid → 5-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]oxindol

HRID 648975Notes

Reaction equation

HRID 648975 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.ClC(OCC(C)C)=O.[N:22]1([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][C:32](=[O:37])[CH2:31]3)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([N:25]1[CH2:26][CH2:27][N:22]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][C:32](=[O:37])[CH2:31]3)[CH2:23][CH2:24]1)=[O:8]

Participants

5

Reactant 3

HCID 7121Veratric AcidHCID 62365Isobutyl chloroformateHCID 136460305-(1-Piperazinyl)oxindol

Product 1

HCID 136460325-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]oxindolYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3,4-Dimethoxybenzoic acid (2.6 g) and 1.65 g of 1,8-diazabicyclo[5,4,0]undecene-7 were added to 100 ml of DMF and to the mixture was added dropwise 1.5 ml of isobutyl chloroformate with ice-cooling externally with stirring. After completion of addition, the mixture was stirred for 30 minutes. To the mixture was added 40 ml of DMF solution containing 2.16 g of 5-(1-piperazinyl)oxindol and the mixture was stirred at room temperature for 5 hours. After completion of reaction, the solvent was removed by distillation. The residue was extracted with 300 ml of chloroform and the extract was washed with a diluted aqueous solution of sodium hydrogencarbonate, water, diluted hydrochloric acid and water, successively. Chloroform was removed by distillation and the residue was recrystallized from methanol to give 1.6 g of 5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]oxindol.

Workup

  1. temperaturecooling externally
  2. additionAfter completion of addition
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringthe mixture was stirred at room temperature for 5 hours
  5. customAfter completion of reaction
  6. customthe solvent was removed by distillation
  7. extractionThe residue was extracted with 300 ml of chloroform
  8. washthe extract was washed with a diluted aqueous solution of sodium hydrogencarbonate, water, diluted hydrochloric acid and water
  9. customChloroform was removed by distillation
  10. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-53877a868641433d93c264f19bd83c78
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

Loading…