2-Bromoethanol → 1-(2-Hydroxyethyl)-4-methylpiperazine

HRID 454251Notes

Reaction equation

HRID 454251 reaction equation
Br[CH2:2][CH2:3][OH:4].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][CH2:3][CH2:2][N:9]1[CH2:10][CH2:11][N:6]([CH3:5])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromoethanol (2.36 g, 19 mmol) was added dropwise to a mixture of 1-methylpiperazine (1.26 g, 13 mmol) and potassium carbonate (5.0 g, 36 mmol) in absolute ethanol (150 ml) and the mixture heated at reflux for 18 hours. The mixture was allowed to cool and the precipitates were removed by filtration and the solvent volatiles were removed by evaporation. The residue was treated with acetone/methylene chloride, the insolubles were removed by filtration and the solvent was removed from the filtrate by evaporation to give 4-(2-hydroxyethyl)-1-methylpiperazine (870 mg, 48%) as a light brown oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. temperatureto cool
  4. customthe precipitates were removed by filtration
  5. customthe solvent volatiles were removed by evaporation
  6. additionThe residue was treated with acetone/methylene chloride
  7. customthe insolubles were removed by filtration
  8. customthe solvent was removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-4fb0bfb863a04905923c54c9e8975167
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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