Potassium Carbonate → 1-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidine

HRID 2243582Notes

Reaction equation

HRID 2243582 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:15])[CH:9]=1.Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:10]([F:15])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 230870721-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potasium carbonate (1.7 g, 12 mmol) was added to a solution of 4-bromo-2-fluorophenol (1.00 g, 5.24 mmol) and 1-(2-chloroethyl)piperidine hydrochloride (0.965 g, 5.24 mmol) in acetonitrile (25 mL). The reaction mixture was heated at reflux for 2 days and then cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown oil. Purification via column chromatography on silica gel (gradient elution with 20-100% ethyl acetate-hexane) afforded 1-(2-(4-bromo-2-fluorophenoxy)ethyl)piperidine 200 as a brown oil. MS (MH+) 302; Calculated 301 for C13H17BrFNO.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 days
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a brown oil
  10. customPurification via column chromatography on silica gel (gradient elution with 20-100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-44548ed14d2548af96f5ce933415f039
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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