2-Bromoethanol → 2-[4-(2-Fluoroethyl)piperazin-1-YL]ethanol

HRID 916481Notes

Reaction equation

HRID 916481 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.OC(C(F)(F)F)=O.[F:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].BrCCO.BrC(O)C>C(#N)C>[F:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:4][CH2:2][OH:1])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 14202443Ethanol, 1-bromo-HCID 87238377HCID 87238377, compound

Product 1

HCID 450996492-[4-(2-Fluoroethyl)piperazin-1-YL]ethanolYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1-(2-Fluoroethyl)piperazine diTFA salt (464 mg, 1.29 mmol), (prepared as described for the starting material in Example 27), was dissolved in acetonitrile (3.5 ml). Potassium carbonate (889 mg, 6.44 mmol) and 2-bromoethanol (95 μl, 1.34 mmol) were added and the mixture heated to 85° C. and left overnight. More bromoethanol (95 μl, 1.34 mmol) was added and the reaction mixture heated at 85° C. for a further 2 hours. The reaction mixture was cooled, filtered and concentrated. The residue was purified by column chromatography eluting with methylene chloride/methanol (saturated with ammonia) (92/8) to give 2-[4-(2-fluoroethyl)piperazin-1-yl]ethanol (151 mg, 66%).

Workup

  1. temperaturethe reaction mixture heated at 85° C. for a further 2 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (saturated with ammonia) (92/8)

Sources & evidence

ORD record
ord-8ef5f226b33742daa00b5744de1794bc
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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