反应详情

To a solution of 4-nitro-3-(piperidin-1-yl)pyridine 1-oxide (1.0 equiv.) in ethanol, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 15 hours. At this time LC/MS analysis indicated that the nitro was reduced to the amine, but the N-oxide was remaining. More 10% palladium on carbon (0.2 eq.) was added and the mixture was resubmitted to a balloon atmosphere of hydrogen. After stirring for 24 hours, more 10% palladium on carbon (0.2 eq.) was added and the mixture was resubmitted to a balloon atmosphere of hydrogen. After stirring for an additional 3 days the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding 3-(piperidin-1-yl)pyridin-4-amine (73%). LCMS (m/z): 178.0 (MH+); LC Rt=1.66 min.

1. stirringAfter stirring for 24 hours
2. stirringAfter stirring for an additional 3 days the mixture
3. filtrationwas filtered through a pad of celite
4. washeluting with methanol
5. customThe volatiles were removed in vacuo