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Novel method for preparing vortioxetine

A technology of vortioxetine and compounds, applied in the field of new process synthesis, can solve the problems of unfavorable industrialization, rare raw materials, cumbersome steps, etc., and achieve the effect of quality, environmental protection, economy, easy access to raw materials, and high quality

Inactive Publication Date: 2016-05-04
万全万特制药(厦门)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Inspecting the above synthetic routes and preparation methods, although the process is constantly being optimized, there are still disadvantages such as rare raw materials, cumbersome steps, low yield and difficult purification, which are not conducive to industrialization

Method used

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  • Novel method for preparing vortioxetine
  • Novel method for preparing vortioxetine
  • Novel method for preparing vortioxetine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 5.0 g of o-nitroiodobenzene (compound VI) and 15.0 g of reduced iron powder into the reaction flask, then add 25 ml of DMF to dissolve, stir until completely dissolved, add 50 ml of concentrated hydrochloric acid dropwise, and heat to reflux after dropping. After 2 hours, the system was suction-filtered while it was hot, and the filtrate was spin-dried to obtain 4.36 g of a light yellow solid, namely o-aminoiodobenzene (compound V), with a yield of 99.2%.

Embodiment 2

[0034] Dissolve 4.36 g of o-aminoiodobenzene (compound V) in 43.6 mL of toluene, add 9.3 g of N,N-bis-(2-chloroethyl)methylamine and 8.72 g of sodium carbonate, stir and raise the temperature to reflux, and monitor by TLC. After the reaction was complete, the temperature was lowered, washed with water and saturated saline, separated, and the organic phase was spin-dried to obtain an oily substance, stirred with n-hexane to precipitate a solid, filtered with suction, and the filter cake was dried to obtain 5.13g, which was 1-(2-iodophenyl) -4-methylpiperazine (compound IV), yield 84.9%.

Embodiment 3

[0036] Dissolve 5.13g of 1-(2-iodophenyl)-4-methylpiperazine (compound IV) in 25mL of DMF, add 1.54g of potassium carbonate, and heat to 55-60°C. Add 2,4-dimethylthiophenol to the system, and react at a temperature of 80-90°C for 4 hours, and monitor the disappearance of the raw material point by TLC. After the reaction was completed, 75 mL of deionized water was added to the system. During the cooling and stirring process, an off-white solid gradually precipitated out. After cooling down to room temperature, it was suction-filtered, the filter cake was washed twice with methanol, and dried to obtain 4.22 g of an off-white solid, which was 1-[2 -(2,4-Dimethylphenylsulfanyl)-phenyl]methylpiperazine (compound III), yield 85.0%.

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Abstract

The invention relates to a novel method for preparing vortioxetine. Reduction, nucleophilic substitution and coupling are conducted on a 2-nitroiodobenzene compound, and a compound of 1-[2-(2,4-dimethyl phenyl sulfanyl)-phenyl]methyl piperazine; then the obtained compound reacts with phenyl chloroformate to obtain 1-[2-(2,4-dimethyl phenyl sulfanyl)-phenyl]piperazine-1-carboxylic acid phenyl ester which generates vortioxetine after being hydrolyzed under the alkaline condition.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a new process synthesis technology of vortioxetine. Background technique [0002] Vortioxetine is a new type of antidepressant drug developed by Lundbeck of Denmark and Takeda Pharmaceutical of Japan. In September 2013, the drug was approved by the US Food and Drug Administration (FDA) under the trade name Brintellix. The drug is a 5-HT3, 5-HT7, 5-HT1D receptor antagonist, a 5-HT1B receptor partial agonist, a 5-HT1A receptor agonist, and a 5-HT transporter inhibitor. To antidepressant effect, for the treatment of major depressive disorder in adults. [0003] The chemical name of Vortioxetine is: 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine, and its structural formula is: [0004] [0005] According to the molecular structure of vortioxetine, using the reverse synthesis analysis method, it is concluded that the synthesis of this compound mainly includes t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 李恩民赵国磊
Owner 万全万特制药(厦门)有限公司
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