Sodium Chloride → 1-(4-Hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acid

HRID 2225517

Reaction equation

HRID 2225517 reaction equation
C([O-])=O.[NH4+].C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH3:29])([C:23]([O:25]CC=C)=[O:24])[CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[O:32][CH3:33])C=C.[Cl-].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH3:29])([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[O:32][CH3:33]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 2723923Ammonium formateHCID 53899198Allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 536577511-(4-Hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acidYield 125.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.4 g of bis(triphenylphosphine)palladium dichloride and 5 g of ammonium formate were added to a solution of 1.1 g of allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate (Example 67) in 100 ml of THF. Under an argon stream, the solution was reacted for hours, while it was refluxed. After reaction, 150 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 1.1 g of 1-(4-hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acid (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customUnder an argon stream, the solution was reacted for hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with an aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThereafter, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-e22296aa17354f3abaa1c0380a77b429
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Linked notes

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