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Methyl iodide → 2-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 11480
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인쇄 미리보기

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HRID 11480 반응식
[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15]Br)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].CI.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)C.O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15][NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2
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참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 574798992-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

생성물 1

HCID 574798982-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide수율 41.6%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

Next, 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, 3.5 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g, 11 mmol), methyl iodide (1.6 g, 11 mmol) and 4-(2-aminoethyl)pyridine (0.43 g, 3.5 mmol) were added to the solution, and the mixture was stirred at an external temperature of 75° C. overnight. Water (100 ml) and diethyl ether (100 ml) were added to the reaction mixture, the reaction mixture was distributed, and the diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate. The diethyl ether layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.6 g (40%) of the titled compound as an oily matter.

후처리

  1. washthe diethyl ether layer was washed with water (70 ml) twice
  2. dry with materiala saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate
  3. concentrationThe diethyl ether layer was concentrated under reduced pressure
  4. customthe concentrate was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9c3e5bf933da48958d386228a5bce4fa
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098226B2

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