自由基超快合成莫氯比胺:杂环化学实验室的一个整体活性

IF 2.5 3区 教育学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Elizabeth Carmona-Quintana, Josué Rodríguez-Lozada, Angel Zamudio-Medina* and Marco Franco-Pérez*, 
{"title":"自由基超快合成莫氯比胺:杂环化学实验室的一个整体活性","authors":"Elizabeth Carmona-Quintana,&nbsp;Josué Rodríguez-Lozada,&nbsp;Angel Zamudio-Medina* and Marco Franco-Pérez*,&nbsp;","doi":"10.1021/acs.jchemed.4c0107710.1021/acs.jchemed.4c01077","DOIUrl":null,"url":null,"abstract":"<p >In this work, we present a novel strategy for the synthesis of the widely used antidepressant moclobemide, suitable for implementation in any organic chemistry teaching laboratory. This procedure not only significantly outperforms existing synthetic methods described in the literature but also enables students to understand and manipulate crucial steps in a synthetic route, demonstrating how fundamental chemical concepts can optimize well-established synthetic techniques, potentially influencing industrial practices. Our approach leverages early stage free radical formation to drive a two-step bond cleavage-formation process, proving more energetically efficient than the conventional addition–elimination mechanism typically involved in this synthesis. These modifications not only reduce the reaction time but also increase the yield, achieving up to 90% in just 5 min. Free radicals were generated using a commercially available UV–visible lamp, ensuring the method’s simplicity and cost-effectiveness for widespread adoption in any laboratory setting. The purity and structure of the obtained product were confirmed by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance experiments, mass spectrometry (DART method) measurements, and melting point analysis.</p>","PeriodicalId":43,"journal":{"name":"Journal of Chemical Education","volume":"102 5","pages":"2020–2025 2020–2025"},"PeriodicalIF":2.5000,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ultrafast Synthesis of Moclobemide via Free Radicals: An Integral Activity in the Heterocyclic Chemistry Lab\",\"authors\":\"Elizabeth Carmona-Quintana,&nbsp;Josué Rodríguez-Lozada,&nbsp;Angel Zamudio-Medina* and Marco Franco-Pérez*,&nbsp;\",\"doi\":\"10.1021/acs.jchemed.4c0107710.1021/acs.jchemed.4c01077\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >In this work, we present a novel strategy for the synthesis of the widely used antidepressant moclobemide, suitable for implementation in any organic chemistry teaching laboratory. This procedure not only significantly outperforms existing synthetic methods described in the literature but also enables students to understand and manipulate crucial steps in a synthetic route, demonstrating how fundamental chemical concepts can optimize well-established synthetic techniques, potentially influencing industrial practices. Our approach leverages early stage free radical formation to drive a two-step bond cleavage-formation process, proving more energetically efficient than the conventional addition–elimination mechanism typically involved in this synthesis. These modifications not only reduce the reaction time but also increase the yield, achieving up to 90% in just 5 min. Free radicals were generated using a commercially available UV–visible lamp, ensuring the method’s simplicity and cost-effectiveness for widespread adoption in any laboratory setting. The purity and structure of the obtained product were confirmed by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance experiments, mass spectrometry (DART method) measurements, and melting point analysis.</p>\",\"PeriodicalId\":43,\"journal\":{\"name\":\"Journal of Chemical Education\",\"volume\":\"102 5\",\"pages\":\"2020–2025 2020–2025\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2025-04-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Education\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jchemed.4c01077\",\"RegionNum\":3,\"RegionCategory\":\"教育学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Education","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jchemed.4c01077","RegionNum":3,"RegionCategory":"教育学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

在这项工作中,我们提出了一种新的策略来合成广泛使用的抗抑郁药莫氯比胺,适用于任何有机化学教学实验室的实施。该程序不仅显著优于文献中描述的现有合成方法,而且使学生能够理解和操作合成路线中的关键步骤,展示基本化学概念如何优化已建立的合成技术,从而潜在地影响工业实践。我们的方法利用早期自由基的形成来驱动两步键裂解-形成过程,证明比这种合成中通常涉及的传统加法-消除机制更具能量效率。这些改进不仅缩短了反应时间,而且提高了收率,在短短5分钟内达到90%。自由基是使用市售的紫外-可见光灯产生的,确保了该方法的简单性和成本效益,可在任何实验室环境中广泛采用。所得产物的纯度和结构通过1H和13C核磁共振实验、质谱(DART法)测量和熔点分析得到证实。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Ultrafast Synthesis of Moclobemide via Free Radicals: An Integral Activity in the Heterocyclic Chemistry Lab

Ultrafast Synthesis of Moclobemide via Free Radicals: An Integral Activity in the Heterocyclic Chemistry Lab

In this work, we present a novel strategy for the synthesis of the widely used antidepressant moclobemide, suitable for implementation in any organic chemistry teaching laboratory. This procedure not only significantly outperforms existing synthetic methods described in the literature but also enables students to understand and manipulate crucial steps in a synthetic route, demonstrating how fundamental chemical concepts can optimize well-established synthetic techniques, potentially influencing industrial practices. Our approach leverages early stage free radical formation to drive a two-step bond cleavage-formation process, proving more energetically efficient than the conventional addition–elimination mechanism typically involved in this synthesis. These modifications not only reduce the reaction time but also increase the yield, achieving up to 90% in just 5 min. Free radicals were generated using a commercially available UV–visible lamp, ensuring the method’s simplicity and cost-effectiveness for widespread adoption in any laboratory setting. The purity and structure of the obtained product were confirmed by 1H and 13C nuclear magnetic resonance experiments, mass spectrometry (DART method) measurements, and melting point analysis.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Chemical Education
Journal of Chemical Education 化学-化学综合
CiteScore
5.60
自引率
50.00%
发文量
465
审稿时长
6.5 months
期刊介绍: The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信