Convenient and efficient N-methylation of secondary amines under solvent-free ball milling conditions
© 2024. The Author(s)..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:14 |
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| Enthalten in: |
Scientific reports - 14(2024), 1 vom: 16. Apr., Seite 8810 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Walter, Mikołaj [VerfasserIn] |
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| Links: |
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| Themen: |
Amines |
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| Anmerkungen: |
Date Revised 25.04.2024 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1038/s41598-024-59374-z |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM371166330 |
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| 520 | |a © 2024. The Author(s). | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a N-methylation | |
| 650 | 4 | |a Amines | |
| 650 | 4 | |a Mechanochemistry | |
| 650 | 4 | |a Solvent-free synthesis | |
| 650 | 4 | |a Vibrational ball mill | |
| 700 | 1 | |a Ciupak, Olga |e verfasserin |4 aut | |
| 700 | 1 | |a Biernacki, Karol |e verfasserin |4 aut | |
| 700 | 1 | |a Rachoń, Janusz |e verfasserin |4 aut | |
| 700 | 1 | |a Witt, Dariusz |e verfasserin |4 aut | |
| 700 | 1 | |a Demkowicz, Sebastian |e verfasserin |4 aut | |
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