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

HRID 1820317Notes

Reaction equation

HRID 1820317 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b7c5bd5fac01404d98a4fd643a319664
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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