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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, efficient, 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 efficiency 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.

SUBMITTER: Walter M

PROVIDER: S-EPMC11021465 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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Convenient and efficient N-methylation of secondary amines under solvent-free ball milling conditions.

Walter Mikołaj M Ciupak Olga O Biernacki Karol K Rachoń Janusz J Witt Dariusz D Demkowicz Sebastian S

Scientific reports 20240416 1

In the present work, we report the development of a rapid, efficient, 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 eff ...[more]

PMID: 38627526

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