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Convenient and efficient N-methylation of secondary amines under solvent-free ball milling conditions
Abstract
In the present work, we report the development of a rapid, efcient, and solvent-free procedure for the N-methylation of secondary amines under mechanochemical conditions. After optimization of the milling parameters, a vibrational ball mill was used to synthesize 26 tertiary N-methylated amine derivatives in a short time of 20 min (30 Hz frequency) and high yields ranging from 78 to 95%. An exception was compounds having a hydroxyl group in their structure, for which a decrease in reaction efciency was observed. During our research, we investigated alternate reaction selectivity occurring in compounds able to form ring closure products that are 3,4-dihydro-2H-1,3-benzoxazine derivatives instead of N-methylated products. The liquid-assisted grinding technique has been applied using formalin as a methylating agent and sodium triacetoxyborohydride as a reducing agent in a reductive amination reaction.
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- Accepted or Published Version
- DOI:
- Digital Object Identifier (open in new tab) 10.1038/s41598-024-59374-z
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- Category:
- Articles
- Type:
- artykuły w czasopismach dostępnych w wersji elektronicznej [także online]
- Published in:
-
Scientific Reports
ISSN: 2045-2322 - Language:
- English
- Publication year:
- 2024
- Bibliographic description:
- Walter M., Ciupak O., Biernacki K., Rachoń J., Witt D., Demkowicz S., Convenient and efficient N-methylation of secondary amines under solvent-free ball milling conditions, Scientific Reports, 2024,10.1038/s41598-024-59374-z
- DOI:
- Digital Object Identifier (open in new tab) 10.1038/s41598-024-59374-z
- Sources of funding:
-
- IDUB
- Verified by:
- Gdańsk University of Technology
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