Potassium Carbonate → 4-(p-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine

HRID 26694

반응식

HRID 26694 반응식
[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][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[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][CH2:19][OH:20])[CH2:10][CH2:9]2)=[O:7])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 27244404-(4-Fluorobenzoyl)piperidine

생성물 1

HCID 124044224-(p-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine수율 48.5%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 60.9 g. (0.293 mole) of 4-(4-fluorobenzoyl)piperidine, 46.0 g. (0.31 mole) of 3-bromopropanol and 41.4 g. (0.30 mole) of anhydrous potassium carbonate in 750 ml. of 1-butanol was stirred at reflux for 15 hours. The mixture was filtered, the filtrate concentrated under vacuum and the residual oil was dissolved in acid solution and extracted with benzene. After discarding the benzene layer, the aqueous acid layer was made basic and extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate, the mixture filtered and the filtrate concentrated under vacuum. Anhydrous ether was added to the oily residue and the oil crystallized. The solid which weighed 57.0 g. was washed with ether and filtered. Upon recrystallizing from isopropanol and isopropyl ether, 38.5 g. (48.5%) of product was obtained. A portion (4.0 g.) was recrystallized from petroleum ether to give 2.4 g. of product melting at 105°-110° C.

후처리

  1. additionA mixture of 60.9 g
  2. temperatureat reflux for 15 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated under vacuum
  5. dissolutionthe residual oil was dissolved in acid solution
  6. extractionextracted with benzene
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  9. filtrationthe mixture filtered
  10. concentrationthe filtrate concentrated under vacuum
  11. additionAnhydrous ether was added to the oily residue
  12. customthe oil crystallized
  13. washwas washed with ether
  14. filtrationfiltered
  15. customUpon recrystallizing from isopropanol and isopropyl ether, 38.5 g

출처 및 근거

ORD 기록
ord-4df0c94704fc41bb9975a1687bc4952b
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151285

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