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New N‐permethylations and introduction of deuterium labelled methyl groups into primary and secondary amines
Author(s) -
Giumanini Angelo G.,
Verardo Giancarlo,
Gei Maria H.,
Lassiani Lucia
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580240305
Subject(s) - chemistry , primary (astronomy) , deuterium , hydride , formaldehyde , sodium hydride , homogeneous , aldehyde , medicinal chemistry , organic chemistry , combinatorial chemistry , hydrogen , catalysis , physics , quantum mechanics , astronomy , thermodynamics
The 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 CH 3‐n D n 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.