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Propargyl bromide → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-(2-propinyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 47519
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HRID 47519 반응식
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[CH2:29](Br)[C:30]#[CH:31].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:31][C:30]#[CH:29])[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]
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참가 물질

7

반응물 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2회HCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 121276521-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-(2-propinyl)-1,3-dihydro-2H-benzimidazol-2-one

시약·촉매·용매 2

HCID 6212Chloroform용매
HCID 6228Dimethylformamide용매

실험 절차

1-[1-(1-Methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-di-hydro-2H-benzimidazol-2-one (28 mg) as synthesized by the method of Referential Example 1 was dissolved in 5 ml of dimethylformamide, and to which 2.0 mg of sodium hydride was added under cooling with ice, followed by 30 minutes' stirring. Ten(10) mg of propargyl bromide was added to the reaction liquid which was stirred for further 3 hours at room temperature. After adding saturated aqueous sodium bicarbonate solution and concentrating the reaction liquid, the resulting residue was distributed between saturated aqueous sodium bicarbonate solution and chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1). Thus 11.3 mg of the title compound was obtained as a colorless oil.

후처리

  1. temperatureunder cooling with ice
  2. stirringwas stirred for further 3 hours at room temperature
  3. concentrationconcentrating
  4. customthe reaction liquid
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-dd75cdfd697344ccab8f96882d9483e6
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06699880B1

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