Potassium Carbonate → 4-(Pyridin-4-ylaminomethyl)-piperidin-3-ol

HRID 1351497Notes

Reaction equation

HRID 1351497 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[C:24](Cl)=[C:23](Cl)[N:22]=[C:21](Cl)[C:20]=2Cl)[CH:13]([OH:29])[CH2:12]1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.[Pd]>[N:22]1[CH:21]=[CH:20][C:19]([NH:18][CH2:17][CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH:13]2[OH:29])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 235772743-Hydroxy-4-[(2,3,5,6-tetrachloro-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 221356624-(Pyridin-4-ylaminomethyl)-piperidin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-hydroxy-4-[(2,3,5,6-tetrachloro-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester compound from Step 1 above (1.64 g) and potassium carbonate (6 g) in ethanol (200 mL) was hydrogenated at 60 psi over 1 g of 10% palladium on charcoal for 5 h. The reaction mixture was filtered and the solids washed well with ethanol. The filtrate was evaporated, taken up in 40% MeOH DCM and refiltered. The filtrate was evaporated to give crude 4-(pyridin-4-ylaminomethyl)-piperidin-3-ol product used without further purification in the next step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed well with ethanol
  3. customThe filtrate was evaporated
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-0a8bf320d7844f968f0fce4b0f2320b6
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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