Reactivities of N-nitrosamines against common reagents and reaction conditions
Author(s)
Type
Journal Article
Abstract
The knowledge of the reactivity of N-nitrosamines (NSAs) with common organic reagents in synthesis is essential in determining their presence in pharmaceutical products, if formed and retained during synthesis. In this study, we carried out a comprehensive survey of the Reaxys database for all reactions in which the NSA functional group is consumed. Very different reactivities for different classes of NSAs, e.g., N,N-dialkylnitrosamines and N,N-diphenylnitrosamine, were identified, suggesting substrates which should be included in any future reactivity screening. A classification of NSAs based on their reactivities, and corresponding reagents and transformations, was drawn up based on the data. Furthermore, the survey identified missing areas in the reported reactivities of NSAs with different reagents. This led to an experimental reactivity screening of 8 commercial NSAs with common synthetic reagents in the Mirabilis tool for purge assessment. The results showed Na2S2O4 in 1 M aqueous NaOH at 50 °C to be highly effective at destroying NSAs without damaging other organic compounds.
Date Issued
2024-10-18
Date Acceptance
2024-09-12
Citation
Organic Process Research and Development, 2024, 28 (10), pp.3837-3846
ISSN
1520-586X
Publisher
American Chemical Society
Start Page
3837
End Page
3846
Journal / Book Title
Organic Process Research and Development
Volume
28
Issue
10
Copyright Statement
© 2024 The Authors. Published by American Chemical Society. This publication is licensed under
CC-BY 4.0 .
CC-BY 4.0 .
License URL
Identifier
http://dx.doi.org/10.1021/acs.oprd.4c00217
Publication Status
Published
Date Publish Online
2024-09-18