Methanol → 2-Hydroxy-5-(piperidin-1-yl)benzoic acid

HRID 454484Notes

Reaction equation

HRID 454484 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.CO.O1CCCC1>O1CCOCC1.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][C:10]=1[C:11]([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 66990101Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

Product 1

HCID 669907452-Hydroxy-5-(piperidin-1-yl)benzoic acidYield 90.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution mixture of the obtained benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate (2.2 g) in dioxane (11 mL), ethyl acetate (17 mL), and methanol (5.5 mL), 10% palladium-carbon (1.1 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. Tetrahydrofuran was added to the reaction mixture, and the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 1.1 g of 2-hydroxy-5-(piperidin-1-yl)benzoic acid as a light yellow solid.

Workup

  1. additionwas added
  2. customthe insoluble substance was removed by filtration
  3. customThe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-062839a6232143e1a3c64be6f3b0275a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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