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.
Authors
Additional information
- DOI
- Digital Object Identifier link open in new tab 10.1038/s41598-024-59374-z
- Category
- Publikacja w czasopiśmie
- Type
- artykuły w czasopismach dostępnych w wersji elektronicznej [także online]
- Language
- angielski
- Publication year
- 2024
