Abstract
AbstractThe extension of the N‐permethylation reaction of amines to aromatic amines with strong electron withdrawing substituents in o‐ and p‐ positions is reported. A comparison of this method with other “best” last step synthetic methods reported in literature is given. The reaction could be extended to the syntheses of N‐permethyl‐derivatives of amines of the type CH3‐nDn by use of formaldehyde, dideuteroformaldehyde, sodium borodeuteride and ‐hydride. Label conservation in the reaction is complete: the final step in the reaction involves H− (or D−) transfer from the reducing agent to a reactive species. The MS of the labelled compounds revealed extensive label excange in the ionization chamber. A new homogeneous procedure for the N‐permethylation, especially suited for larger scale preparations, is described.
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