Potassium Carbonate → N-(beta-bromopropionyl)-p-piperazinylaniline

HRID 1649243Notes

Reaction equation

HRID 1649243 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)=[O:5].Br.Br[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)HCID 20480582N-(beta-bromopropionyl)-p-aminoaniline

Product 1

HCID 20480598N-(beta-bromopropionyl)-p-piperazinylanilineYield 29.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 14.0 g of N-(β-bromopropionyl)-p-aminoaniline, 18 g of bis(β-bromoethyl)amine monohydrobromide and 70 ml of methanol was stirred under reflux for 15 hours. After cooling, the reaction mixture was added 3.06 g of potassium carbonate and stirred under reflux for 8 hours. After cooling, crystals which formed were collected by filtration and washed with methanol to give 5.3 g of N-(β-bromopropionyl)-p-piperazinylaniline. Production of the compound was confirmed by IR and NMR spectra.

Workup

  1. temperatureunder reflux for 15 hours
  2. temperatureAfter cooling
  3. stirringstirred
  4. temperatureunder reflux for 8 hours
  5. temperatureAfter cooling
  6. customcrystals which formed
  7. filtrationwere collected by filtration
  8. washwashed with methanol

Sources & evidence

ORD record
ord-f96b17fad8cb4d7e98fb24daffbb71a7
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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