Hydrochloric Acid → HCID 178490538, compound

HRID 2225590Notes

Reaction equation

HRID 2225590 reaction equation
[OH-].[K+].[CH3:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:36])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([C:29]([O:31]CC)=[O:30])[CH2:25][CH2:24]3)=[C:16]([O:34][CH3:35])[CH:15]=2)[CH2:6][CH2:5]1.Cl>CO>[CH3:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:10][C:11](=[O:36])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]3)=[C:16]([O:34][CH3:35])[CH:15]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178469228HCID 178469228, compound

Product 1

HCID 178490538HCID 178490538, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml of 2 M aqueous potassium hydroxide solution was added to a solution of 0.5 g of N-(trans-4-methylcyclohexyl) -4-{2-[4-(ethoxycarbonyl)piperidino]ethoxy}-3-methoxycinnamamide (Example 168) in 50 ml of methanol. The solution was reacted for 1 hours, while it was refluxed. After reaction, 2 N hydrochloric acid to the reaction solution, acidifying the solution. The solution was then extracted twice with 50 ml of methylene chloride. The organic layer obtained was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The product obtained was recrystallized from methanol/ether, yielding 0.43 g of N-(trans-4-methylcyclohexyl)-4-[2(4-carboxypiperidino)ethoxy]-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 1 hours, while it
  2. temperaturewas refluxed
  3. extractionThe solution was then extracted twice with 50 ml of methylene chloride
  4. customThe organic layer obtained
  5. dry with materialwas dried over magnesium sulfate
  6. customThereafter, the solvent was removed in vacuo
  7. customThe product obtained
  8. customwas recrystallized from methanol/ether

Sources & evidence

ORD record
ord-6c0b1f390e2e49fc81e6c33696d585b4
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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