3-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine → 4-(2-pyridinyl)-1-Piperidinepropanamine
Reaktionsgleichung
[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-].[Pd+2].[OH-]>[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]1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
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 palladium hydroxide 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 (30 g) [Note: If a large excess of silica gel is used the recovery of the product will be very low] using methylene chloxidemethanol/2M ammonia in MeOH (90:8:4 to 90:40:40) as eluent. The product was obtained as a pale yellow oil.