Linear Synthesis of 10-Hydroxy-N,N-dimethyl-N-((3-(tosyloxy)pyridin-2-yl)methyl)decan-1-aminium Bromide

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In 2019, carbamates derived from 3-hydroxypyridine were classified as nerve agents and subsequently included in the Annex on Chemicals by the Conference of the States Parties. Herein, we describe the preparation of a structural simulant of this class of compounds, 10-hydroxy-N,N-dimethyl-N-((3-(tosyloxy)pyridin-2-yl)methyl)decan-1-aminium bromide. The compound was synthesized via tosylation of 2-((N,N-dimethylamino)methyl)pyridin-3-ol with tosyl chloride in the presence of sodium hydride, followed by alkylation of the resulting ((N,N-dimethylamino)methyl)pyridin-3-yl 4-methylbenzenesulfonate with 10-bromodecan-1-ol.