1-Benzyl-4-(2-pyridyl)-1,2,3,6-tetrahydropyridine → 2-(Piperidin-4-yl)pyridine

HRID 380484Notes

Reaction equation

HRID 380484 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH3:8].[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 151233351-Benzyl-4-(2-pyridyl)-1,2,3,6-tetrahydropyridine

Product 2

HCID 222AmmoniaHCID 103747502-(Piperidin-4-yl)pyridineYield 179.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.2 g (12.8 mmol) of 1-benzyl-4-(2-pyridyl)-1,2,3,6-tetrahydropyridine and 1.2 g of Pd(OH)2/C in 25 mL of MeOH was hydrogenated at 50 psi for 6 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by chomatography [CH2Cl2:MeOH:(2M NH3 in MeOH), 100:8:4) to give 1.86 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chomatography [CH2Cl2

Sources & evidence

ORD record
ord-6c16622a2cd74f8f94ee0876db76a27d
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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