Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride

Magano J; Akin A; Chen MH; Giza K; Moon J; Saenz J

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Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride

机译：实用合成1-（7-氟-萘-1-基）哌嗪盐酸盐

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A practical and scalable preparation of 1-(7-fluoronaphthalen-1-yl)-piperazine hydrochloride (1) is reported. The original route for the synthesis of this compound involved the use of 1-amino-7-fluoronaphthalene and bis(2-chloroethyl)amine hydrochloride, two highly toxic compounds. A new protocol has been developed that employs a palladium-catalyzed Buchwald-Hartwig cross-coupling reaction between 1-Boc-piperazine and 1-bromo-7-fluoronaphthalene followed by piperazine deprotection with HCl gas. In addition, an efficient palladium removal protocol allowed for the preparation of the target molecule with less than 20ppm of this metal. This methodology has been successfully implemented to produce multigram quantities of 1 with excellent purity and low palladium content.

机译：报道了一种实用且可扩展的1-（7-氟萘-1-基）-哌嗪盐酸盐的制备方法（1）。合成该化合物的原始途径涉及使用1-氨基-7-氟萘和双（2-氯乙基）胺盐酸盐，这两种剧毒化合物。已开发出一种新的方案，该方案采用1-Boc-哌嗪和1-bromo-7-氟萘之间的钯催化的Buchwald-Hartwig交叉偶联反应，然后用HCl气体对哌嗪进行脱保护。另外，有效的钯去除方案允许制备具有少于20ppm的这种金属的目标分子。该方法已成功实施，以产生具有优良纯度和低钯含量的1克多克量。

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来源
《Synthetic Communications》 |2008年第21期|共9页
作者
Magano J; Akin A; Chen MH; Giza K; Moon J; Saenz J;
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正文语种 eng
中图分类有机化学;
关键词
Buchwald-Hartwig coupling; fluoronaphthalene; palladium catalyzed cross-coupling; piperazine;

机译：Buchwald-Hartwig偶联;氟萘;钯催化交叉偶联;哌嗪;

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1. Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride [J] . Synthetic Communications . 2008,第21期

机译：实用合成1-（7-氟-萘-1-基）哌嗪盐酸盐
2. Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride [J] . Magano J, Akin A, Chen MH, Synthetic Communications . 2008,第19a21期

机译：实用合成1-（7-氟-萘-1-基）哌嗪盐酸盐
3. Montmorillonite K10 Catalysed Condensation of 1-(3-Chlorophenyl)-4-(3-chloropropyl) piperazine and 1,2,4-Triazolo [4,3-a]pyridine-3-(2H)-one: A Proficient and Green Synthesis of Trazodone Hydrochloride and Its Analogues [J] . Trimurti L Lambat, Sujata S Deo Synthesis & Catalysis: Open Access . 2016,第1期

机译：蒙脱石K10催化1-（3-氯苯基）-4-（3-氯丙基）哌嗪与1,2,4-三唑并[4,3-a]吡啶-3-（2H）-one的缩合反应盐酸曲唑酮的合成及其类似物
4. Facile synthesis of (R)-1-(1H-indol-3-yl)propan-2-amines hydrochloride from Ketones [C] . Zhi Guang Peng, Yuan Xiang Yao, Dong Hong Yin, China Functional Material Technology and Industry Forum . 2013

机译：从酮酮的（R）-1-（1H-吲哚-3-基）Propan-2-胺氨基的容易合成
5. Tetrahydroisoquinoline and 1-(pyridin-2-Yl)piperazine as Multi-Receptor Probes for CNS Drug Design [D] . Ofori, Edward. 2016

机译：四氢喹啉和1-（Pyridin-2-Y1）哌嗪作为CNS药物设计的多受体探针
6. Exploring the RC-106 Chemical Space: Design and Synthesis of Novel (E)-1-(3-Arylbut-2-en-1-yl)-4-(Substituted) Piperazine Derivatives as Potential Anticancer Agents [O] . Roberta Listro, Silvia Stotani, Giacomo Rossino, 2020

机译：探索RC-106化学空间：设计和合成新型（E）-1-（3-芳基-2-烯-1-基）-4-（取代）哌嗪衍生物作为潜在的抗癌剂
7. Montmorillonite K10 Catalysed Condensation of 1-(3-Chlorophenyl)-4-(3-chloropropyl) piperazine and 1,2,4-Triazolo 4,3-apyridine-3-(2H)-one: A Proficient and Green Synthesis of Trazodone Hydrochloride and Its Analogues [O] . Trimurti L Lambat, Sujata S Deo 2016

机译：Montmorillonite K10催化1-（3-氯苯基）-4-（3-氯丙基）哌嗪和1,2,4-三唑的吡啶-3-（2H） - 酮：熟练和绿色的凝胶胺盐酸曲酮的合成及其类似物

Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride

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