Potassium Carbonate → 1-(3-(Trifluoromethyl)pyridin-2-YL)piperidin-4-one

HRID 1394092노트

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HRID 1394092 반응식
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].O1[C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[O:21]CC1>CS(C)=O.C(OCC)C>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([N:25]2[CH2:26][CH2:27][C:22](=[O:21])[CH2:23][CH2:24]2)=[N:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decane3회HCID 5898332-Chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 219047511-(3-(Trifluoromethyl)pyridin-2-YL)piperidin-4-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

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온도
100 °C

실험 절차

2-Chloro-3-(trifluoromethyl)pyridine (11.92 g, 65.7 mmol)), K2CO3(19.10 g, 138 mmol), and 1,4-dioxa-8-azaspiro[4.5]decane (8.85 mL, 69.0 mmol) were combined in DMSO (65 mL) and stirred at 100° C. for 3 hours. The mixture was treated with additional 1,4-dioxa-8-azaspiro[4.5]decane (2.0 mL, 16 mmol), stirred for 2 hours, treated with additional 1,4-dioxa-8-azaspiro[4.5]decane (1.0 mL, 7.8 mmol), and stirred for 1 hour. The mixture was diluted with diethyl ether (200 mL), washed with water (250 mL), washed with brine (100 mL), dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in concentrated HCl (25 mL), stirred for 3 hours, basified with concentrated NH4OH, extracted with CH2Cl2, and the phases separated. The organic phase was dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified via flash chromatography (20% to 40% diethyl ether/hexanes) to provide the title compound.

후처리

  1. stirringstirred for 2 hours
  2. stirringstirred for 1 hour
  3. washwashed with water (250 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in concentrated HCl (25 mL)
  9. stirringstirred for 3 hours
  10. extractionextracted with CH2Cl2
  11. customthe phases separated
  12. dry with materialThe organic phase was dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationthe filtrate concentrated under reduced pressure
  15. customThe residue was purified via flash chromatography (20% to 40% diethyl ether/hexanes)

출처 및 근거

ORD 기록
ord-39286539d6464bbbac22797bc9ac148f
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348343B2

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