Acetic Acid → 5-(Piperidin-1-yl)pyridin-2-amine

Temperature

45 °C

To 6′-Nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (0.25 g) in THF (8 mL) was added iron (0.539 mg) and water (2.5 mL). Then acetic acid (0.35 mL) was added dropwise and the mixture was allowed to stir at 45° C. for 12 hours. TLC analysis confirmed complete consumption of the starting material. The suspension was filtered through celite and the filter cake was washed well with ethyl acetate. The filtrate was concentrated in vacuo prior to addition of 2N NaOH. The aqueous layer was saturated with NaCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4 and evaporated to give a residue that was purified by flash chromatography on silica gel (gradient of MeOH in DCM containing 0.5% NH4OH). 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine was obtained as a black oil (0.196 g). MS (ESI): 178.1 (MH+).

1. customconsumption of the starting material
2. filtrationThe suspension was filtered through celite
3. washthe filter cake was washed well with ethyl acetate
4. concentrationThe filtrate was concentrated in vacuo
5. additionto addition of 2N NaOH
6. extractionextracted with ethyl acetate
7. washThe organic phase was washed with brine
8. dry with materialdried over Na2SO4
9. customevaporated
10. customto give a residue that
11. customwas purified by flash chromatography on silica gel (gradient of MeOH in DCM containing 0.5% NH4OH)

ORD record

ord-d66f5d56d17c4e448e756ebe11f43e43

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482341B2