Triethylamine → N-[1-[2-(1-Ethylcyclohexyl)ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide

HRID 1820317노트

반응식

HRID 1820317 반응식
C(N(CC)CC)C.[CH2:8]([C:10]1([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)[CH2:20][CH2:19]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:9].[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](Cl)=[O:38].[Cl-].[NH4+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:8]([C:10]1([CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([N:24]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)[C:37]([C:33]3[O:32][CH:36]=[CH:35][CH:34]=3)=[O:38])[CH2:22][CH2:23]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH3:9]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 682422-Furancarbonyl chlorideHCID 231099031-[2-(1-Ethylcyclohexyl)ethyl]-4-(5-methylpyridin-2-yl)aminopiperidine

생성물 1

HCID 11452995N-[1-[2-(1-Ethylcyclohexyl)ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide수율 90.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.33 mL, 9.55 mmol) was added to a solution of 1-[2-(1-ethylcyclohexyl)ethyl]-4-(5-methylpyridin-2-yl)aminopiperidine (1.31 g, 3.98 mmol) in methylene chloride (13 mL). After adding 2-furoyl chloride (0.47 mL, 4.78 mmol) while cooling on ice, the mixture was stirred for 2 hours. A 25% aqueous ammonium chloride solution was added to the reaction mixture, extraction was performed with chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (80 g NH silica Chromatorex DM2035, hexane:ethyl acetate=2:1) to obtain the title compound as a light yellow solid (1.52 g, 3.59 mmol) (90% yield).

후처리

  1. temperaturewhile cooling on ice
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (80 g NH silica Chromatorex DM2035, hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-b7c5bd5fac01404d98a4fd643a319664
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601843B2

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