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Method for synthesizing evodiamine

A technology of evodial alkaloid and a synthesis method, applied in directions such as organic chemistry, can solve problems such as cost cannot be effectively controlled, large environmental pollution, unsuitable for industrialized production, etc. Effect

Active Publication Date: 2011-01-12
HANGZHOU FST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process uses phosphorus oxychloride, which causes great environmental pollution and is not suitable for modern industrial production. Moreover, the total yield of evodiamine prepared by this method is only up to 44%. The cost cannot be effectively controlled, and it is not suitable for industrial production.

Method used

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  • Method for synthesizing evodiamine
  • Method for synthesizing evodiamine
  • Method for synthesizing evodiamine

Examples

Experimental program
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Embodiment 1

[0036] Example 1 Preparation of tryptamine I

[0037] Indole acetonitrile (15.6g, 0.1mol) was dissolved in 100ml methanol, put into the hydrogenation kettle, add 2.0g Pd / C (5%), seal the kettle, N 2 After the replacement, feed hydrogen gas, react at room temperature for 24 hours, until no hydrogen is absorbed, the reaction solution is suction filtered to the concentration tank to concentrate methanol, and 100ml of ethyl acetate is added, cooled, separated, and centrifuged to obtain tryptamine I (quantitative yield) .

Embodiment 2

[0038] Example 2 Preparation of tryptamine I

[0039] Indole acetonitrile (15.6g, 0.1mol) was dissolved in 100ml ethanol, put into the hydrogenation kettle, add 2.0g Pd / C (5%), seal the kettle, N 2 After the replacement, pass in hydrogen, raise the temperature to 50°C and react for 12 hours until no hydrogen is absorbed. After cooling, filter the reaction solution to the concentration kettle to concentrate ethanol, add 100ml of ethyl acetate, cool, separate the material, and centrifuge to obtain tryptamine I (quantitative yield).

Embodiment 3

[0040] Example 3 Preparation of Tryptamine I

[0041] Indole acetonitrile (15.6g, 0.1mol) was dissolved in 100ml DMF, put into the hydrogenation kettle, add 2.0g Pd / C (5%), seal the kettle, N 2 After the replacement, pass in hydrogen, raise the temperature to 100°C and react for 2 hours until no hydrogen is absorbed. After cooling, filter the reaction solution to the concentration kettle to concentrate DMF, add 100ml of ethyl acetate, cool, precipitate, and centrifuge to obtain tryptamine I 13g, yield 85%.

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Abstract

The invention discloses an organic chemical synthesis method, in particular a method for chemically synthesizing evodiamine. Indole acetonitrile is taken as a raw material, and the method comprises the following steps of: performing catalytic hydrogenation on palladium carbon to prepare tryptamine; mixing with ethyl formate to form solution for a formylation reaction, and dissolving the reactants in solution of dichloromethane; adding trifluoroacetic acid for cyclization, and preparing another intermediate in a reflux state from N-methylanthranilic acid and excessive ethyl chloroformate; and finally, subjecting two intermediates to condensation reaction in a non-polar solvent system. The method for chemically synthesizing the evodiamine has the advantages of rich raw material source, low price of the raw material, capacities of improving the yield and fulfilling the aim of reducing the production cost by optimizing reaction conditions, environmental friendliness and suitability for large-scale industrial production. The product can be widely applied to pharmaceutical industry.

Description

technical field [0001] The invention relates to the field of organic chemistry and medicinal chemistry, in particular to a chemical synthesis method of evodiamine. technical background [0002] Evodiamine is the active ingredient in the fruits of Rutaceae plants Evodia rutaecarpa, Shihu, and Evodiamine laxatives. Bitter taste, afraid of heat, low toxicity. It can manage the loose bags, soothe the liver and relieve pain. It has the functions of lowering blood pressure, inhibiting platelet aggregation, anti-inflammation and bronchoconstriction, regulating body temperature, and losing weight. At present, all the products on the market are Chinese medicinal products of Evodia rutaecarpa. [0003] The chemical name of evodiamine is 8,13,13b,14-tetrahydro-14-methylindole[2′,3′;3,4]pyrido[2,1-b]quinpyridine-5(7H )-ketone. Its chemical structural formula is: [0004] [0005] Molecular formula is C 19 h 17 N 30 , the molecular weight is 303.36. [0006] In 1915, Asahina ...

Claims

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Application Information

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IPC IPC(8): C07D471/14
Inventor 吴永龙徐竹清陈长荣徐伟
Owner HANGZHOU FST PHARMA
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