2-Bromoethanol → 2-[4-(3-Bromo-phenyl)-piperidin-1-yl]-ethanol

HRID 491205Notes

Reaction equation

HRID 491205 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 214952014-(3-Bromophenyl)piperidine

Product 1

HCID 575164902-[4-(3-Bromo-phenyl)-piperidin-1-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Bromo-phenyl)-piperidine (1.2 g, 4.8 mmol) and 2-bromoethanol (0.72 mL, mmol) were diluted with DMF (20 mL) and treated with potassium carbonate (2.7 g, 20 mmol). These were stirred at ambient temperature for 18 then poured onto water and extracted with ethyl acetate. Organic phase then washed with brine, dried over sodium sulfate, filtered and evaporated to clear oil (0.6 g, 44%).

Workup

  1. additionthen poured onto water
  2. extractionextracted with ethyl acetate
  3. washOrganic phase then washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to clear oil (0.6 g, 44%)

Sources & evidence

ORD record
ord-a650b9ebc4244226bdd88bf3f837c996
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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