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

HRID 1858713노트

반응식

HRID 1858713 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-e5fbebd9d98346838082ac8e4774129f
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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