Sodium Carbonate → 4-(3,4,5-Trimethoxyphenyl)piperazine monohydrobromide

HRID 621554Notes

Reaction equation

HRID 621554 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].Br.[Br:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[Na+].[Na+]>CO>[BrH:15].[CH3:13][O:12][C:8]1[CH:7]=[C:5]([N:6]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 322853,4,5-TrimethoxyanilineHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 128994224-(3,4,5-Trimethoxyphenyl)piperazine monohydrobromideYield 114.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18.3 grams of 3,4,5-trimethoxyaniline and 31.2 g of bis(β-bromoethyl)amine monohydrobromide are mixed with 170 ml of methanol and refluxed by heating under a nitrogen gas stream for 10 hours. After cooling the reaction mixture, 5.3 g of anhydrous sodium carbonate are added to the mixture and refluxed by heating for additional 10 hours. Under reduced pressure, about 70 ml of methanol are removed off by distillation, and the mixture is allowed to staand to cool at room temperature. The crystals thus precipitated are collected by filtration and washed with a small amount of ethanol. Recrystallization from ethanol obtains 38 g of 4-(3,4,5-trimethoxyphenyl)piperazine monohydrobromide in the form of colorless plate-like crystals with a melting point of 227°-228° C.

Workup

  1. temperaturerefluxed
  2. temperatureby heating under a nitrogen gas stream for 10 hours
  3. additionare added to the mixture
  4. temperaturerefluxed
  5. temperatureby heating for additional 10 hours
  6. customUnder reduced pressure, about 70 ml of methanol are removed off by distillation
  7. customThe crystals thus precipitated
  8. filtrationare collected by filtration
  9. washwashed with a small amount of ethanol
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0dc35eb64ce44d778f5973616b6240bd
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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