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Chemical synthesis method for oxcarbazepine

A chemical synthesis and catalyst technology, which is applied in the field of chemical synthesis of oxcarbazepine, can solve the problems of low yield, unfavorable industrial production, environmental safety hazards and large cyanide, and achieve high reaction yield, no three wastes, and product purity Good results

Active Publication Date: 2008-12-03
ZHEJIANG UNIV OF TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problem of this process is the use of cyanide, which has great environmental and safety risks.
2. Using carbamazepine as raw material to synthesize oxcarbazepine (JP2004175761) through oxidative rearrangement, the reaction mainly has a low yield, which is not conducive to industrial production

Method used

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  • Chemical synthesis method for oxcarbazepine
  • Chemical synthesis method for oxcarbazepine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Feeding amount 5-cyano-11-nitro-5H dibenzoazepine (hereinafter referred to as raw material III) 26.3g (0.1mol), the consumption of Raney nickel is 0.263g (0.01 times for the quality of raw material III), organic Solvent is toluene, and its consumption is 10 times of raw material III quality, and hydrogen pressure is 5 atmospheres.

[0028] Put the above materials into a 500mL autoclave reactor, replace the air three times, pass hydrogen to reach the specified pressure, raise the temperature to 40°C, and perform a reduction reaction for 5 hours. After the reaction is completed, filter and wash the filter residue with a solvent twice the mass of the raw material III , the filtrates were combined, the amount of concentrated hydrochloric acid was added dropwise to 8.3mL (0.1mol), and the reaction was kept for 5 hours, concentrated under reduced pressure until the solvent was basically evaporated, added 50mL of water, cooled to 5°C-10°C and allowed to stand for crystallizatio...

Embodiment 2

[0030] Feeding amount 5-cyano group-11-nitro-5H dibenzoazepine (III) 26.3g (0.1mol), the consumption of Raney nickel is 0.02 times of raw material III quality, and organic solvent is toluene, and its consumption is raw material 2 times of the quality of III, the hydrogen pressure is 10 atmospheres, and the mole of HCl in the concentrated hydrochloric acid is 0.8 times of the mole of raw material III.

[0031] The reduction reaction temperature was reflux temperature, the reduction reaction time was 4 hours, and the hydrolysis reaction time was 5 hours. Other operations were the same as in Example 1 to obtain 23.2 g of oxcarbazepine with a product yield of 92.0% and a purity of 99.1%.

Embodiment 3

[0033] Feeding amount 5-cyano group-11-nitro-5H dibenzoazepine (III) 26.3g (0.1mol), the consumption of Raney nickel is 0.10 times of raw material III quality, organic solvent is dichloromethane, its consumption It is 8 times of the mass of the raw material III, the hydrogen pressure is 15 atmospheres, and the mole number of HCl in the concentrated hydrochloric acid is 1.2 times of the mole number of the raw material III.

[0034] The reduction reaction temperature was reflux temperature, the reduction reaction time was 2 hours, and the hydrolysis reaction time was 5 hours. Other operations were the same as in Example 1 to obtain 21.6 g of oxcarbazepine with a product yield of 85.7% and a purity of 98.8%.

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Abstract

The invention discloses a chemical synthesis method of oxcarbazepine, which comprises the steps as follows: adding 5-cyan-11-nitro-5H Dibenzoyl nitrogen heterocyclic shown in formula (III), Raney's nickel catalyst and organic solvent to a reactor, charging hydrogen till the pressure of the hydrogen reaches 2-20atm, performing the reduction reaction completely at 40-120 DEC C, filtering to obtain the filtrate, adding 20wt%-36.5wt% of hydrochloric acid for hydrolyzing completely, concentrating the reactant, and cooling for crystallization to obtain oxcarbazepine shown in formula (I). The reaction equation is described as follows. The synthetic route has the advantages of advanced technological line, simple and safe operation, higher product yield and purity and wide industrialized prospect.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of oxcarbazepine. (2) Background technology [0002] Oxcarbazepine is a ketone derivative of carbamazepine. It is a new type of antiepileptic drug developed in recent years. Its curative effect on epilepsy is better than that of carbamazepine, and there is no cross adverse reaction when it is used in combination with other antiepileptic drugs. In the past few years, some countries in the world have used oxcarbazepine to replace carbamazepine clinically in the treatment of intractable epilepsy, intractable trigeminal neuralgia and emotional disorders, and achieved good therapeutic effects. Before the present invention provides, the chemical synthesis method of relevant oxcarbazepine mainly is: 1. take 10-methoxy-iminostilbene as raw material method, react with sodium cyanate (or cyanic acid) acylation, hydrolysis, obtain Oxcarbazepine (IN 2004MU00663, PCT2005092862). The main problem that this p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/22A61P25/08
CPCC07D223/26C07D223/28A61P25/08
Inventor 苏为科李坚军蒋祖林徐健康宋刚
Owner ZHEJIANG UNIV OF TECH
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