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1 Polish Journal of Chemistry

1 2008

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Transformation of Tertiary Amines into Alkylating Reagents by Treatment with 2-Chloro-4,6-dimethoxy-1,3,5-triazine. A Synthetic Application of Side-Reaction Accompanying Coupling by Means of 4-(4,6-Dimethoxy-[1,3,5]triazin-2-yl)-4-methyl-morpholin-4-ium

Kolesińska B., Kamiński Z. J.

Polish Journal of Chemistry

2008

Vol. 82, nr 11

2115-2123

Mild reaction conditions are described for the preparation of a number of alkyl chlorides and 2-dialkyl(aryl)amino-4,6-dimethoxy-1,3,5-triazines by dealkylation of quaternary triazinylammonium chlorides formed as reactive intermediates in reaction of tertiary amines with 2-chloro-4,6-dimethoxy-1,3,5-triazine. The high selectivity of substitution was observed within the reactivity order of the alkyl groups: benzyl ~ allyl > methyl > n-alkyl. Studies on dealkylation of S-(-)-dimethyl-(1-phenylethyl)amine to R-(+)-1-chloro-1-phenylethane revealed that reaction proceeded with an inversion of configuration on the carbon atom as may be expected for SN2 type substitution. The scope of reaction was extended by exchange of anion in quaternary triazinylammonium chlorides with I-, SCN-, C6H5O-, CH3COO- followed by N-dealkylation step.