N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine, sertraline imine (3), is an intermediate for the synthesis of Zoloft, sertraline hydrochloride (1). A cleaner, simpler, and more efficient alternative to the Schiff base-mediated formation of sertraline imine has been developed and is presented in this paper. The condensation reaction between 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalone, sertraline tetralone (2), and monomethylamine was carried out in ethanol, without the need for classical dehydrating agent, such as TiCl4, or more novel approaches, such as molecular sieves, both of which produce hazardous byproducts and solid wastes. The low solubility of the imine 3 in this type of solvent is exploited, such that the reaction equilibrium favorably enhances the imine formation. Furthermore, an improved and highly selective catalytic reduction of 3 with Pd/CaCO3 catalyst in ethanol as the reaction solvent, followed by the resolution of the racemic cis isomer (6) with d-(−)-...

中文翻译：

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N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine 的一种新的和简化的制备方法和合成 (1S-cis)-4- 的望远镜方法(3,4-二氯苯酚)-1,2,3,4-四氢-N-甲基-1-萘胺扁桃酸盐：合成盐酸舍曲林的关键中间体

N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine, sertraline imine (3)，是合成唑洛夫特，盐酸舍曲林 (1) 的中间体。已经开发出一种更清洁、更简单、更有效的替代席夫碱介导的舍曲林亚胺形成的方法，并在本文中进行了介绍。4-(3,4-二氯苯基)-3,4-二氢-1(2H)-萘、舍曲林四氢萘酮(2)和一甲胺之间的缩合反应在乙醇中进行，无需传统的脱水剂，如如 TiCl4，或更新颖的方法，如分子筛，这两种方法都会产生有害的副产品和固体废物。利用了亚胺 3 在此类溶剂中的低溶解度，使得反应平衡有利地增强了亚胺的形成。此外，