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

HRID 2223935Notes

Reaction equation

HRID 2223935 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3([CH2:22][CH2:23][OH:24])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38](Cl)=[O:39].[OH-].[K+]>O1CCCC1.O.CO>[OH:24][CH2:23][CH2:22][C:16]1([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=3)[C:38]([C:34]3[O:33][CH:37]=[CH:36][CH:35]=3)=[O:39])[CH2:13][CH2:12]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 682422-Furancarbonyl chlorideHCID 597150012-[4-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]tetrahydropy-ran-4-yl]ethanol

Product 1

HCID 59714878N-[1-[2-[4-(2-Hydroxyethyl)tetrahydropyran-4-yl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]tetrahydropy-ran-4-yl]ethanol (synthesized in Example 80) (239 mg) in tetrahydrofuran (3 mL) was added triethylamine (0.29 mL) and 2-furoyl chloride (0.17 mL) sucessively. The reaction solution was stirred at room temperature for 30 minutes. To the reaction solution were added methanol (4 mL) and a 3N aqueous potassium hydroxide solution (2 mL). The reaction solution was stirred at room temperature for additional 15 minutes. 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, chloroform-methanol (30:1)] to give the title compound (210 mg).

Workup

  1. stirringThe reaction solution was stirred at room temperature for additional 15 minutes
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, chloroform-methanol (30:1)]

Sources & evidence

ORD record
ord-9293436ceaa54d83b8faafc1843296ab
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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