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Ethyl Acetate → tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate

HRID 75105
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인쇄 미리보기

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HRID 75105 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:3][CH:4]=1
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 27364342-Bromo-5-(trifluoromethyl)pyridine

생성물 1

HCID 58576452tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate수율 83.3%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of 0.678 g (3 mmol) of 2-bromo-5-(trifluoromethyl)pyridine, 0.901 g (4.5 mmol) of tert-butyl 4-aminopiperidine-1-carboxylate and 0.829 g (6 mmol) of potassium carbonate in 5 ml of dimethyl sulphoxide is heated at 100° C. for 20 hours. The mixture is cooled to ambient temperature and then 50 ml of ethyl acetate and 15 ml of water are added. The organic phase is separated by settling and washed twice with 15 ml of water and then with 15 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated under vacuum. The product is purified by chromatography on silica gel, elution being carried out with a 20:80 and then 30:70 mixture of ethyl acetate and cyclohexane in order to obtain 0.864 g (2.5 mmol) of product in the form of a white solid.

후처리

  1. temperatureThe mixture is cooled to ambient temperature
  2. customThe organic phase is separated
  3. washwashed twice with 15 ml of water
  4. dry with materialIt is dried over sodium sulphate
  5. customevaporated under vacuum
  6. customThe product is purified by chromatography on silica gel, elution
  7. addition30:70 mixture of ethyl acetate and cyclohexane in order

출처 및 근거

ORD 기록
ord-9d9fb918e31e49c8ae43b43b85cd4bb9
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835418B2

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