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

HRID 1820317ノート

反応式

HRID 1820317 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b7c5bd5fac01404d98a4fd643a319664
出典データセット
uspto-grants-2009_10
特許番号
US07601843B2

反応ノート

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