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Cesium carbonate → {1-[3-(1-Quinolin-2-yl-piperidin-4-yl)-pyrazin-2-yl]-piperidin-4-yl}-methanol

HRID 1850345
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HRID 1850345 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)[CH2:4][CH2:3]1.Cl[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)[CH2:6][CH2:7]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 67469206[1-(3-Piperidin-4-YL-pyrazin-2-YL)-piperidin-4-YL]-methanol hydrochloride

생성물 1

HCID 58547302{1-[3-(1-Quinolin-2-yl-piperidin-4-yl)-pyrazin-2-yl]-piperidin-4-yl}-methanol수율 70.47%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a solution of [1-(3-piperidin-4-yl-pyrazin-2-yl)-piperidin-4-yl]-methanol hydrochloride (156 mg, 0.5 mmol) and 2-chloro-quinoline (81.5 mg 0.5 mmol) in DMF (5 mL) was added Cs2CO3 (325 mg, 1 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (15 mL) and brine (15 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give {1-[3-(1-quinolin-2-yl-piperidin-4-yl)-pyrazin-2-yl]-piperidin-4-yl}-methanol (142 mg, 0.35 mmol, yield 70.47%).

후처리

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (15 mL) and brine (15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-cb5422ffb557424eac9cec61905dacd0
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957073B2

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