Potassium Carbonate → N-[1-[2-[1-[2-[3,5-Bis(hydroxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

HRID 2223914Notes

Reaction equation

HRID 2223914 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:41]=[C:42]([CH2:44][O:45]C(=O)C)[CH:43]=1)[O:9][CH2:10][CH2:11][C:12]1([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([N:26]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[CH2:22][CH2:21]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:41]=[C:42]([CH2:44][OH:45])[CH:43]=1)[O:9][CH2:10][CH2:11][C:12]1([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([N:26]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[CH2:22][CH2:21]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69144599N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Product 1

HCID 59715008N-[1-[2-[1-[2-[3,5-Bis(hydroxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamideYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (276 mg) dissolved in methanol (4 mL) was added potassium carbonate (11 mg). The solution was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with chloroform-ethanol (80:20). The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (228 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionSaturated aqueous sodium bicarbonate solution was added to the solution, and it
  3. extractionwas extracted with chloroform-ethanol (80:20)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-58a2da11c9734fa59050ab670ba73eb3
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…