3-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine → 4-(2-pyridinyl)-1-Piperidinepropanamine

HRID 1167689Notes

Reaction equation

HRID 1167689 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH:12]=1>CO.[OH-].[OH-].[Pd+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 184761423-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine

Product 1

HCID 101768154-(2-pyridinyl)-1-PiperidinepropanamineYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(3′,6′-Dihydro-2′-H-[2,4′]bipyridinyl-1′-yl)-propylamine (3.48 g crude, 15.9 mmol) in MeOH (40 mL), was added 1.0 g of Pearlman's catalyst. The suspension was hydrogenated under 120 psi for 10 h after which the reaction mixture was filtered through a pad of celite and the solvent was removed. The residue was purified by column chromatography over silica gel using CH2Cl2/methanol/2M NH3 in MeOH (90:8:4 to 90:40:40) as the eluting system. The product was obtained as a pale yellow oil (3.21 g, 91%).

Workup

  1. filtrationafter which the reaction mixture was filtered through a pad of celite
  2. customthe solvent was removed
  3. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-254c40fc047d40a6af25c592129da115
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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