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Preparation method of 1-[2-(2,4-dimethyl phenylsulfanyl)-phenyl]piperazine

A technology for protecting groups and compounds, which is applied in the synthesis field of preparing 1-[2--phenyl]piperazine, can solve problems such as the generation of coupling impurities and difficult purification, and achieve easy purification, high yield and low cost. Effect

Active Publication Date: 2014-10-22
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The patent protects the above-mentioned route from many factors such as solvent, alkali and palladium source used; the key point is that the patent uses a variety of heavy metal catalysts of palladium, and in drug synthesis, its heavy metals, especially palladium, need to be strictly limited More importantly, the use of patented synthesis methods will lead to the generation of other coupling impurities during the reaction process, which will bring difficulties to subsequent purification

Method used

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  • Preparation method of 1-[2-(2,4-dimethyl phenylsulfanyl)-phenyl]piperazine
  • Preparation method of 1-[2-(2,4-dimethyl phenylsulfanyl)-phenyl]piperazine
  • Preparation method of 1-[2-(2,4-dimethyl phenylsulfanyl)-phenyl]piperazine

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Embodiment 1

[0018]

[0019] Compound II (2-(2,4-dimethylphenylsulfanyl)-aniline) (45.87 g, 0.2 mol), bis(2-chloroethyl)amine hydrochloride (46.4 g, 0.26 mol) , potassium carbonate (55.0g, 0.4mol), potassium iodide (33mg, 0.2mmol) were added to acetonitrile (500ml), heated under reflux for 24h, filtered while hot, the filtrate was stirred at room temperature, crystallized, filtered with suction, and the filter cake was washed with acetonitrile , the filter cake was vacuum-dried at 40 °C for 10 h to obtain compound I (white solid, 46.57 g) with a molar yield of 78%. Melting point: 116~118°C, HPLC: 98.3%. LC / MS (m / z) 299 (MH+), NMR consistent with the above structure.

Embodiment 2

[0021] Compound II (2-(2,4-dimethylphenylsulfanyl)-aniline) (22.93 g, 0.1 mol), bis(2-chloroethyl)amine hydrochloride (23.2 g, 0.13 mol) , potassium carbonate (27.5g, 0.2mol), potassium iodide (16.5mg, 0.1mmol) were added to n-butanol (300ml), heated to reflux for 24h, filtered while hot, slowly cooled to room temperature, crystallized, filtered, filter cake Washed with acetonitrile, the filter cake was vacuum dried at 40 °C for 10 h to obtain compound I (white solid, 35.8 g) with a molar yield of 60%.

Embodiment 3

[0023] Compound II (2-(2,4-dimethylphenylsulfanyl)-aniline) (22.93 g, 0.1 mol), bis(2-chloroethyl)amine hydrochloride (23.2 g, 0.13 mol) , potassium carbonate (27.5g, 0.2mol), potassium iodide (16.5mg, 0.1mmol) were added to ethyl acetate (300ml), heated under reflux for 24h, filtered while hot, slowly cooled to room temperature, added a little seed crystal for crystallization, After filtration, the filter cake was washed with ethyl acetate, and the filter cake was vacuum-dried at 40 °C for 10 h to obtain compound I (white solid, 32.8 g) with a molar yield of 54.9%.

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Abstract

The invention relates to a preparation method of 1-[2-(2,4-dimethyl phenylsulfanyl)-phenyl]piperazine. The method includes in the presence of an alkali and a catalyst, a compound II and a compound III are subjected to a reaction in an organic solvent to generate the compound I. The preparation method provided by the invention has no need of use of a palladium catalyst, and has the advantages of low cost, high yield, easy purification, and easy industrialization.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, in particular to a low-cost, green and environment-friendly synthesis method for preparing 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine. Background technique [0002] 1-[2-(2,4-Dimethylphenylsulfanyl)-phenyl]piperazine is a diaryl sulfide amine, and its hydrobromide (Lu AA21004, Vortioxetine Hydrobromide) is a class of New chemical antidepressant; used primarily to treat depression and anxiety disorders. This product was jointly developed by Lundbeck and Takeda. In 2012.09, the MAA application for depression was submitted in Europe through the centralized review process; in 2012.10, the NDA application for the treatment of adult major depressive disorder (MDD) was submitted in the United States. In the patent WO03029232, the compound is disclosed and protected by the patent; in the divisional patent CN102617513A of WO2007144005, the preparation method of the compound is s...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCY02P20/55C07D295/096
Inventor 戚郜飞杜祖银任帆游军辉
Owner JIANGSU HANSOH PHARMA CO LTD
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