Methanol → 4-(2,4-Dihydroxyphenyl)piperidine-1-carboxylic acid pyridin-2-ylamide

HRID 2070071Notes

Reaction equation

HRID 2070071 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][C:17]=2[O:30]CC2C=CC=CC=2)[CH2:12][CH2:11]1)=[O:9].CO>C(OCC)(=O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[OH:30])[CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 67421889HCID 67421889, compound

Product 1

HCID 462143804-(2,4-Dihydroxyphenyl)piperidine-1-carboxylic acid pyridin-2-ylamideYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

20 mg of 4-(2,4-Bis(benzyloxy)phenyl)piperidine-1-carboxylic acid pyridin-2-ylamide are dissolved in 20 ml of ethyl acetate and then 1 ml of methanol is added. 10 mg of palladium-on-charcoal at 10% are added, and then the reaction mixture is stirred for 18 hours under a hydrogen atmosphere. The mixture is filtered and the residue is then crystallized from an ethyl acetate/heptane mixture. 5 mg of 4-(2,4-dihydroxyphenyl)piperidine-1-carboxylic acid pyridin-2-ylamide. Yield: 39%

Workup

  1. filtrationThe mixture is filtered
  2. customthe residue is then crystallized from an ethyl acetate/heptane mixture

Sources & evidence

ORD record
ord-9afd97b7ee374546931967439c069719
Source dataset
uspto-grants-2012_10
Patent number
US08299259B2

Reaction notes

Loading…