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Synthesis method suitable for industrialized production of vortioxetine hydrobromide

A kind of vortioxetine hydrobromide, suitable technology, applied in the field of drug synthesis, can solve the problems of unfavorable industrial production, low yield, cumbersome operation, etc., and achieve the effect of simple operation, high yield and good reaction selectivity

Active Publication Date: 2014-11-05
ANHUI HEALSTAR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0023] This method has been greatly improved compared with the previous method, but it is still cumbersome to operate, the yield is low, and the production requires high pressure at the same time, which is not conducive to industrial production (Chinese Journal of Pharmaceutical Industry, 2014, 45 (4), 301-302)

Method used

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  • Synthesis method suitable for industrialized production of vortioxetine hydrobromide
  • Synthesis method suitable for industrialized production of vortioxetine hydrobromide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] a. Preparation of Intermediate II:

[0046] 111g (1.0mol) of o-fluoroaniline and 327g (1.5mol) of Boc anhydride were stirred and refluxed in 2200ml of dry tetrahydrofuran for 48h, and the end point of the reaction was identified by TLC (developing solvent: dichloromethane-n-pentane=1:4), and the reaction was completed , cooled to room temperature, filtered, the filtrate was concentrated to dryness, the residue was added petroleum ether 1500ml, vigorously stirred for 30min, left to stand, the supernatant liquid was poured off, the residue was concentrated to dryness to obtain 205g colorless oil intermediate II, the yield 97.1%.

[0047] 1 H—NMR (500MHz, CDCl 3 / TMS,ppm):

[0048] δ 8.13 (m, 1H), 7.50 (m, 1H), 7.29 (m, 1H), 7.00 (bs, 1H), 6.89 (m, 1H), 1.54 (s, 9H).

[0049] b. Preparation of Intermediate III:

[0050]Intermediate II 190g (0.90mol), 2,4-dimethylthiophenol 125g (0.90mol) and DMF 1500ml, DIPEA (N,N-diisopropylethylamine) 149ml (0.91mol); at 85-90 Stir...

Embodiment 2

[0064] a. Preparation of Intermediate II:

[0065] 111g (1.0mol) of o-fluoroaniline and 327g (1.5mol) of Boc anhydride were stirred and refluxed in 2000ml of dry tetrahydrofuran for 48h, and the end point of the reaction was identified by TLC (developing solvent: dichloromethane-n-pentane=1:4), and the reaction was completed , cooled to room temperature, filtered, the filtrate was concentrated to dryness, the residue was added petroleum ether 2000ml, stirred vigorously for 30min, left to stand, the supernatant liquid was poured off, the residue was concentrated to dryness to obtain 201g colorless oil intermediate II, the yield 96.3%.

[0066] b. Preparation of Intermediate III:

[0067] Intermediate II 190g (0.90mol), 2,4-dimethylthiophenol 125g (0.90mol) and DMF 2000ml, DIPEA (N,N-diisopropylethylamine) 149ml (0.91mol); at 80-85 Stir at ℃ for 36 hours, TLC to identify the reaction end point (developing agent: dichloromethane-n-pentane = 1:3), after the reaction is completed...

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Abstract

The invention provides a novel method for preparing vortioxetine hydrobromide, and belongs to the technical field of medicine synthesis. The method uses 2-fluoroaniline as a starting material to prepare the clinical medicinal vortioxetine hydrobromide by Boc protection, condensation, deprotection condensation, cyclization and other 4 steps of reaction. The method has the advantages of easy obtained raw material, low price, simple synthesis operation, mild reaction condition, easy control, no high pressure, good reaction selectivity, high yield and suitability for industrial production.

Description

technical field [0001] The present invention relates to a method for producing antidepressants, in particular to a method for industrialized production of antidepressant vortioxetine hydrobromide, and to a new synthesis method for vortioxetine hydrobromide, which belongs to the pharmaceutical industry The field of synthetic technology. Background technique [0002] Major depressive disorder is a disabling mental illness characterized by altered mood, interference with work, sleep, study, eating and recreation, loss of interest in daily activities, insomnia or excessive sleeping, restlessness, agitation, fatigue, feelings of guilt Or feelings of uselessness, difficulty thinking or concentrating, suicidal thoughts, etc., but the symptoms of patients are not all the same. There are a variety of medications that patients can choose from based on how they respond to the medications. Six randomized clinical trials conducted in the United States and other countries have shown tha...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 徐奎刘丽
Owner ANHUI HEALSTAR PHARM CO LTD
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