Triethylamine → N-[1-[2-[1-(2-Hydroxyethyl)cyclooctyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

HRID 2223932Notes

Reaction equation

HRID 2223932 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3([CH2:24][CH2:25][OH:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40](Cl)=[O:41].[OH-].[K+]>O1CCCC1.O.CO>[OH:26][CH2:25][CH2:24][C:16]1([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:27])=[CH:6][CH:5]=3)[C:40]([C:36]3[O:35][CH:39]=[CH:38][CH:37]=3)=[O:41])[CH2:9][CH2:10]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 682422-Furancarbonyl chlorideHCID 597148642-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclooctyl]ethanol

Product 1

HCID 59714852N-[1-[2-[1-(2-Hydroxyethyl)cyclooctyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclooctyl]ethanol (synthesized in Example 73) (0.53 g) in tetrahydrofuran (7 mL) were added triethylamine (0.79 mL) and 2-furoyl chloride (0.35 mL) successively. The solution was stirred at room temperature for 1 hour. To the reaction solution was added methanol (7 mL) and a 3N aqueous potassium hydroxide solution (4.7 mL), and it was stirred at room temperature for 15 hours. Water was added to the reaction solution and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, methanol-chloroform (5:95)] to give the title compound (0.55 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography [silica gel, methanol-chloroform (5:95)]

Sources & evidence

ORD record
ord-299d420232464db5acfdf9fb027e5c2c
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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