New N-Permethylations and Introduction of Deuterium Labelled Methyl Groups into Primary and Secondary Amines

The extension of the N-permethylation reaction of amines to aromatic amines with strong electron withdrawing substituets in o- and p-positions is reported. The reaction could be extended to the syntheses of N-permethyl-derivatives of amines of the type CH3-nDn by the use of formaldehyde, dideuteroformaldehyde, sodium borodeuteride and -hydride. Label conservation in the reaction is complete. The MS of the labelled compounds revealed extensive label exchange in the ionization chamber.