Diisopropylethylamine → 4-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

HRID 730827노트

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HRID 730827 반응식
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[F:16][C:15]([F:18])([F:17])[C:14]1[C:9]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[N:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 471744384-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of piperazin-2-one (4.85 g, 48.47 mmol, Avocado Research), 2-chloro-3-trifluoromethyl-pyridine (8.8 g, 48.47 mmol, TCI America) and diisopropylethylamine (11 mL, 58.16 mmol, Aldrich) in DMSO (160 mL) was heated at 120° C. for 16 h. The mixture was cooled to room temperature, diluted with H2O (500 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with dichloromethane/MeOH (15:1) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 206 (M+1).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane/MeOH (15:1)

출처 및 근거

ORD 기록
ord-2173b642f10942b68982dc1ad14f91f5
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582761B2

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