Benzyl Bromide → 1-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine

HRID 1858713Notes

Reaction equation

HRID 1858713 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=2)=[CH:11][CH:10]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH2:21]([N:18]1[CH2:17][CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 100615101-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

13.8 g (100 mmol) of potassium carbonate were added to a solution of 10.0 g (46.8 mmol) of 4-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridine hydrochloride in 400 ml of ethanol and the reaction mixture was subsequently heated to reflux temperature. A solution of 5.8 ml (49 mmol) of benzyl bromide in 100 ml of ethanol was added dropwise within one hour and thereafter the mixture was stirred at this temperature for a further 1 hour. The reaction mixture was cooled to room temperature and filtered, the filtrate was extracted with water and ethyl acetate and finally the organic phase was dried over magnesium sulphate. After evaporation in a water-jet vacuum the crude product obtained was chromatographed on silica gel with hexane and ethyl acetate as the eluent. There were obtained 8.90 g (71% of theory) of 1-benzyl-4-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridine; MS: 267 (M)+.

Workup

  1. temperaturethe reaction mixture was subsequently heated
  2. temperatureto reflux temperature
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with water and ethyl acetate
  5. dry with materialfinally the organic phase was dried over magnesium sulphate
  6. customAfter evaporation in a water-jet vacuum the crude product
  7. customobtained
  8. customwas chromatographed on silica gel with hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e5fbebd9d98346838082ac8e4774129f
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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