Synthesis Of Substituted Piperidine N-oxides

Hepatitis B virus (HBV) is a chronic disease in the world and can induce serious liver pathological changes. The most widely used medicine at present is Lamivudine and Interfron, which have some side effects. Based on our previous discovery, we have designed and synthesized four new amine oxide compounds as candidates of new anti-HBV reagents.Amination of N-methyl piperidone with aniline, p-methyl aniline, 1-naphthylamine, o-methyloxylaniline respectively yielded four amino-substituted piperidines. After acetylization of the four amino-substituted piperidines, we got 1-methyl-4-(N-acetyl-N-phenyl)aminopiperidine, 1-methyl-4-(N-acetyl-N-p-methyl- phenyl)aminopiperidine, 1-methyl-4-(N-acetyl-N-1-naphyl)aminopiperidine and 1-methyl-4-(N-acetyl-N-o-methyloxylphenyl)aminopiperidine. Oxidations of these piperidines with H2O2 in ethanol, yielded 1-methyl-4-(N-acetyl-N-phenyl) amino-1-oxypiperidine, 1-methyl-4-(N-acetyl-N-p-methylphenyl)amino-1-oxypiperi- dine, 1-methyl-4-(N-acetyl-N-1-naphyl)amino-1-oxypiperidine and 1-methyl-4-(N- acetyl-N-o-methyloxylphenyl)amino-1-oxypiperidine.The structures of these compounds were characterized by IR and 1H-NMR.