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Preparation method of votistine hydrobromide midbody

A technology of vortioxetine hydrobromide and intermediates, which is applied in the field of drug synthesis, can solve the problems of unfavorable safety and environmental protection, long reaction time, poor product quality, etc., to reduce safety and environmental risks, suitable for industrial production, and product quality controllable effect

Inactive Publication Date: 2018-04-17
CHONGQING ZEN PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction time is 72 hours, the reaction time is long and the reaction is incomplete; and the reaction temperature is high, which is not conducive to safety and environmental protection; at the same time, the product is not refined, and the product quality is poor

Method used

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  • Preparation method of votistine hydrobromide midbody
  • Preparation method of votistine hydrobromide midbody
  • Preparation method of votistine hydrobromide midbody

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Preparation of 1-tert-butoxycarbonyl-4-[2-(2,4-dimethylphenylsulfanyl)phenyl]-3,5-dioxopiperazine (Intermediate C)

[0034] Put 233.9g of dicyclohexylcarbodiimide, 4.26g of 4-dimethylaminopyridine, and 500ml of dichloromethane into a 3L three-necked flask, stir at 20~30°C for 30min, and dissolve 100g of intermediate B in 600ml of dichloromethane In the medium, control the temperature at 20~30°C and slowly drop it in. After the dropping, react for 60~70min. After the reaction is complete, add 1000ml of 2N hydrochloric acid to wash, wash with 1000ml of saturated sodium bicarbonate, evaporate the organic layer to dryness under reduced pressure, add 1500ml of ethanol, and heat up to Stir at 73~80°C for 15~25min, cool down to 0~5°C, filter with suction, and dry under reduced pressure at 40°C to obtain 160.3g of off-white crystalline powder with a purity of 99.354% and a yield of 86.18%.

[0035] HPLC Detection Conditions

[0036]

[0037]

Embodiment 2

[0038] Example 2 Preparation of 1-tert-butoxycarbonyl-4-[2-(2,4-dimethylphenylsulfanyl)phenyl]-3,5-dioxopiperazine (Intermediate C)

[0039] Put 145g of bisisopropylcarbodiimide, 4.50g of 4-dimethylaminopyridine, and 500ml of ethyl acetate into a 3L three-necked flask, stir at 20~30°C for 30min, and dissolve 106g of intermediate B in 600ml of ethyl acetate , control the temperature at 20~30℃ and slowly drop it into the three-necked flask. After the dropping, react for 60~70min. , heated to 60-65°C, stirred for 15-25min, cooled to 0-5°C, filtered with suction, and dried under reduced pressure at 40°C to obtain 165.8g of off-white crystalline powder with a purity of 99.318% and a yield of 89.14%.

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Abstract

The invention discloses a preparation method of votistine hydrobromide midbody. The preparation method includes steps of using a midbody B or 2-(2, 4-dimethyl phenyl sulfenyl) aniline as a raw material, and reacting with N-Boc-iminodiacetic acid in non-proton solvent under the effect of condensating agent; after completing reaction, performing concentration, extraction, concentration and refiningto obtain the 1-tert-butoxy carbonyl-4-[2-(2, 4-dimethyl phenyl sulfenyl) phenyl]-3, 5-dioxo piperazine with high purity and high yield, or a midbody C namely. The whole synthetic process has the advantages of low raw material cost, low solvent toxicity, short reaction time, high product yield and good quality, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and relates to a vortioxetine hydrobromide intermediate 1-tert-butoxycarbonyl-4-[2-(2,4-dimethylphenylthio)phenyl]- The preparation method of 3,5-dioxopiperazine is an important intermediate product of vortioxetine hydrobromide. Background technique [0002] Severe depressive disorder is a kind of emotional dysfunction caused by the abnormality of the genetic system (gene) in the individual patient, or the great changes in the acquired environment, and a series of depressive symptoms mainly characterized by persistent and spontaneous depression. The disease can threaten people's life safety, induce physical diseases, cause people to have negative emotions, and deprive people of social functions. Great burden on individuals and society. [0003] Vortioxetine hydrobromide was jointly developed by Japan's Takeda Pharmaceutical and Denmark's Lundbeck Pharmaceuticals. It is indicate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/08
CPCC07D241/08
Inventor 王飞徐天帅邓祥林代毅李大明黄超明仝佳琪叶大伟
Owner CHONGQING ZEN PHARMACEUTICAL CO LTD
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