2-Bromoethanol → 4-(4-Fluorobenzoyl)-1-(2-hydroxyethyl)piperidine

HRID 2457

Reaction equation

HRID 2457 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19]>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]2)=[O:7])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 148921654-(4-Fluorobenzoyl)-1-(2-hydroxyethyl)piperidineYield 78%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In an atmosphere of argon, 4-(4-fluorobenzoyl)piperidine (2.07 g, 10 mmol) was dissolved in triethylamine (30 ml) to which was subsequently added dropwise 2-bromoethanol (1.1 ml, 14.7 mmol) at room temperature. After 1 hour of heating under reflux, triethylamine was removed by evaporation, and the resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml) and extracted with ethyl acetate. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate-methylene chloride:methanol=10:1) to obtain 1.96 g (78.0%) of the title compound in the form of light yellow solid.

Workup

  1. temperatureAfter 1 hour of heating
  2. temperatureunder reflux
  3. customtriethylamine was removed by evaporation
  4. additionthe resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml)
  5. extractionextracted with ethyl acetate
  6. dry with materialThe resulting organic layer was dried on anhydrous sodium carbonate
  7. customthe solvent was removed by evaporation
  8. customthe resulting residue was purified

Sources & evidence

ORD record
ord-b2d3298a193f4e188fb14350c59014ca
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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