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

HRID 2085433Notes

Reaction equation

HRID 2085433 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>[OH-].[OH-].[Pd+2].CO>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9]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

A suspension of 3-(3′,6′-dihydro-2′-H-[2,4′]bipyridinyl-1′-yl)-propylamine (3.48 g crude, 15.9 mmol) and Pearlman's catalyst (1.0 g) in MeOH (40 mL) 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 (30 g) [Note: If a large excess of silica gel is used the recovery of the product will be very low] (CH2Cl2/methanol/2M NH3 in MeOH, 90/8/4 to 90/40/40). The product was obtained as a pale yellow oil (3.21 g, 91%). 1H NMR δ (CD3OD) 1.50-1.99 (m, 10 H), 2.02-2.06 (m, 2 H), 2.37-2.75 (m, 3 H), 3.02-3.06 (br m, 2 H), 7.05-7.09 (m, 4 H), 7.16 (dt, J=0.9 Hz, J=8.7 Hz, 1 H), 8.48 (dd, J=0.9 Hz, J=4.2 Hz, 1 H).

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 (30 g) [

Sources & evidence

ORD record
ord-c0b7d0bb4a494b4e80ffe0227dd4ede1
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

Loading…