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

HRID 18410
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HRID 18410 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 to distribute it. The diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give the target compound (0.6 g, 40%) 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, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationThen the obtained concentrate
  5. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b3013360acf7497db699e1a1d3e6ad1d
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741346B2

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