摘要:
Bipyridines were reduced to piperidinylpyridines in modest yield using nickel-aluminum alloy in potassium hydroxide solution. The reduction was selective, and 3-substituted rings were reduced in preference to 4-substitution in preference to 2-substitution. Thus 2,3-bipyridine gave only 2-(3'-piperidinyl)pyridine, 2,4-bipyridine gave only 2-(4'-piperidinyl)pyridine, and 3,4-bipyridine gave only 4-(3'-piperidinyl)pyridine. The symmetrial 2,2'- and 4,4'-bipyridines also gave the corresponding piperidinylpyridines, but the reduction of 3,3'-bipyridine was too sluggish to be practical. The products were identified using C-13 NMR spectrospy, and the C-13 NMR spectra of the starting bipyridines were also recorded.