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Water → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

HRID 1446512
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HRID 1446512 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[CH:8]=O.C([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:28])(=O)C.O>C1COCC1.CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)/[CH:8]=[C:24]1/[C:23](=[O:28])[NH:22][CH2:27][CH2:26][CH2:25]/1
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참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 118159051-Acetylpiperidin-2-oneHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

생성물 1

HCID 58548909(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one수율 36.4%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
2회
HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a sodium hydride suspension (40% mineral oil content, 2.77 g) in THF (50 mL) and DMF (200 mL), a solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (10 g) obtained in Example 1 and 1-acetylpiperidin-2-one (7.17 g) in THF (50 mL) and DMF (200 mL) were added dropwise over 20 minutes at 5° C. This reaction solution was agitated at 0° C. for 2 hours. The reaction solution was added to iced water and the reaction solution was extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, and concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The deposited solids were separated by filtering and 5.0 g of the title compound was obtained by washing with diethyl ether. The physical properties of the compound are as follows.

후처리

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. dry with materialafter dried over anhydrous magnesium sulfate
  5. customThe deposited solids were separated
  6. filtrationby filtering

출처 및 근거

ORD 기록
ord-6b262135470e4d27b3066015f905eb85
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07667041B2

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