Collect. Czech. Chem. Commun.
1995, 60, 1536-1540
https://doi.org/10.1135/cccc19951536
New Method for Preparation of 1-Azabicyclo[2.2.2]octane-4-carbonitrile and 1-Azabicyclo[3.2.2]nonane-5-carbonitrile
Jiří Svoboda and Jaroslav Paleček
Institute of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
Abstract
The title compounds were prepared from pyridine-4-carboxamide. Its alkylation with 2-chloroethanol or 3-chloropropanol, followed by hydrogenation gave 1-substituted piperidine-4-carboxamides IIIa and IIIb, respectively, which on treatment with thionyl chloride were converted into the respective 1-substituted halogenoalkylpiperidine-4-carbonitriles IVa and IVb. On cyclization, compounds IVa and IVb afforded 1-azabicyclo[2.2.2]octane-4-carbonitrile and 1-azabicyclo[3.2.2]nonane-5-carbonitrile, respectively.
