Water → 1-Benzyl-4-(pyridin-3-YL)piperidin-4-OL

HRID 1005207

반응식

HRID 1005207 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>COC(C)(C)C>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([OH:26])([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 122863-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

생성물 1

HCID 10940791-Benzyl-4-(pyridin-3-YL)piperidin-4-OL수율 60%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매2회

반응 조건

온도
-75 °C

실험 절차

(α) A solution of 16.7 g (106 mmol) of 3-bromo-pyridine in 200 ml of tert-butyl methyl ether was cooled to -75° C. Thereto there was added dropwise within 45 minutes a solution of 66 ml (106 mmol) of n-butyllithium (1.6M in hexane) and the mixture was stirred at -75° C. for one hour. Subsequently, a solution of 10.0 g (52.8 mmol) of 1-benzyl-4-piperidone in 50 ml of tert-butyl methyl ether was added dropwise at -70° C. to -75° C. and thereafter the mixture was stirred for 2 hours. Subsequently, the mixture was left to warm to room temperature. Thereafter, it was hydrolyzed with 50 ml of water and extracted with 100 ml of ethyl acetate. The organic phase was dried over magnesium sulphate and finally the solvent was evaporated under reduced pressure, with the product beginning to separate. From the evaporated mother liquor there were isolated by crystallization from a mixture of ethyl acetate and hexane a further 1.9 g, so that a total of 8.4 g (60% of theory) of 1'-benzyl-2',3',5',6'-tetrahydro-1'H-[3,4']bipyridinyl-4'-ol were obtained as a colourless solid; MS: 268 (M+H)+.

후처리

  1. stirringthe mixture was stirred for 2 hours
  2. waitSubsequently, the mixture was left
  3. temperatureto warm to room temperature
  4. extractionextracted with 100 ml of ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customfinally the solvent was evaporated under reduced pressure, with the product
  7. customto separate
  8. customFrom the evaporated mother liquor there were isolated by crystallization from a mixture of ethyl acetate and hexane a further 1.9 g

출처 및 근거

ORD 기록
ord-3e831f5dfbfa4c19868461769383e172
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051712

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