Sodium Carbonate → 5-(1-Piperazinyl)oxindol.hydrobromide

HRID 648972Notes

Reaction equation

HRID 648972 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.Br.[Br:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[BrH:13].[N:1]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27732135-Amino-2-oxindoleHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 136460315-(1-Piperazinyl)oxindol.hydrobromideYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-aminooxindol (14 g), 29 g of bis(β-bromoethyl)amine.hydrobromide in 250 ml of ethanol was stirred under reflux for 8 hours and allowed to stand overnight at room temperature. To the mixture was added sodium carbonate (10.1 g) and the mixture was stirred further for 8 hours under reflux. After cooling to room temperature, crystals which precipitated were collected by filtration and recrystallized from a mixture of water and ethanol to give 16 g of 5-(1-piperazinyl)oxindol.hydrobromide.

Workup

  1. temperatureunder reflux for 8 hours
  2. stirringthe mixture was stirred further for 8 hours
  3. temperatureunder reflux
  4. customcrystals which precipitated
  5. filtrationwere collected by filtration
  6. customrecrystallized from a mixture of water and ethanol

Sources & evidence

ORD record
ord-6edf5b510ab443ce936951097c188da6
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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