The conformational analysis of heterocyclic systems. Part VIII. Kinetics of quaternisation of N-alkylpiperidines and N-alkylpiperazines in acetonitrile
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 556-562
- https://doi.org/10.1039/j29660000556
Abstract
Rates of reaction are reported for series of 1-alkyl-4-phenylpiperidines and 1-alkyl-4-t-butylpiperazines with methyl iodide in acetonitrile solution at –35 to +40°. The results are compared with rates for quinazolines (from the literature) and 2-methyl-2-aza-adamantane and N-methyltropane. The proportions of the isomeric quaternary salts formed have been determined by n.m.r. spectroscopy. It is concluded that 1-alkyl-4-phenylpiperidines and 1-alkyl-4-t-butylpiperazines undergo predominant equatorial alkylation except in the case of the N-t-butyl derivatives.Keywords
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