2-Bromoethanol → 2-(4-Ethylpiperazin-1-yl)ethan-1-ol

HRID 706541Notes

Reaction equation

HRID 706541 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][OH:18]>C(#N)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:16][CH2:17][OH:18])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 791961-Ethylpiperazine

Product 1

HCID 189851542-(4-Ethylpiperazin-1-yl)ethan-1-olYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethylpiperazine (5.0 g, 43.8 mmol) was dissolved in 90 mL of acetonitrile, followed by the addition of powdered potassium carbonate (18.2 g, 131 mmol), and 2-bromoethanol (10.9 g, 87.6 mmol). This mixture was warmed to reflux for 16 hours, cooled to ambient temperature, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (10% MeOH/DCM/0.5% NH4OH) to give 5.4 g (78%) of 2-(4-ethylpiperazin-1-yl)ethanol as a light yellow oil.

Workup

  1. temperatureThis mixture was warmed
  2. temperatureto reflux for 16 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography (10% MeOH/DCM/0.5% NH4OH)

Sources & evidence

ORD record
ord-b0cc7d33f54a4532a72ad523e20c1595
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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