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Preparation method of 5-methoxytryptamine

A technology of methoxytryptamine and methoxy, which is applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, great environmental hazards, unfavorable industrial production operations, etc., and achieve the effect of simple operation

Pending Publication Date: 2022-03-25
阜阳欣奕华制药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of 5-methoxytryptamine involves complicated procedures and harsh reaction conditions. The raw materials and reagents used are more harmful to the environment, and the highly toxic substance phosgene carbonyl chloride and the flammable and explosive substance lithium aluminum hydride are used, which is not conducive to industrialization. production operation

Method used

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  • Preparation method of 5-methoxytryptamine
  • Preparation method of 5-methoxytryptamine
  • Preparation method of 5-methoxytryptamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The present embodiment provides a kind of preparation method of 5-methoxytryptamine, the preparation method of described 5-methoxytryptamine comprises the following steps:

[0064] The synthetic route is:

[0065]

[0066] (1) Add 4-methoxyphenylhydrazine hydrochloride (250g, 1.43mol), ethanol (750g), 30% hydrochloric acid (75g , 0.62mol), under stirring, add 4-chlorobutyraldehyde dimethyl acetal (250g, 1.64mol) at one time, heat up to 75°C, react for 12h, TLC shows that the reaction is complete, stop heating, cool down to 55°C, concentrate under reduced pressure Obtain 600g of concentrated solution, the purity of 3-(2-haloethyl)-5-methoxyl-1H-indole in this concentrated solution is 98.2%;

[0067] (2) In a 5L autoclave with stirring and a thermometer, add the concentrated solution (300g) obtained in step (1), ethanol (900g), 27% ammonia water (480g), check that the seal is good, stir evenly, and heat up to 85°C After 12 hours of reaction, heating was stopped, the ...

Embodiment 2

[0071] The present embodiment provides a kind of preparation method of 5-methoxytryptamine, the preparation method of described 5-methoxytryptamine comprises the following steps:

[0072] The synthetic route is:

[0073]

[0074] (1) Add 4-methoxyphenylhydrazine hydrochloride (500g, 2.86mol), ethanol (1500g), 32% hydrochloric acid (150g , 1.24mol), under stirring, add 4-chlorobutyraldehyde dimethyl acetal (500g, 3.25mol) at one time, heat up to 70°C, react for 13h, TLC shows that the reaction is complete, stop heating, cool down to 50°C, concentrate under reduced pressure Obtain 1252g of concentrated solution, the purity of 3-(2-haloethyl)-5-methoxyl-1H-indole in this concentrated solution is 98.5%;

[0075] (2) In a 5L autoclave with stirring and a thermometer, add the concentrated solution (600g) obtained in step (1), ethanol (1800g), 25% ammonia water (960g), after checking that the seal is good, stir evenly, and heat up to 80°C , after reacting for 13 hours, stop heat...

Embodiment 3

[0079] The present embodiment provides a kind of preparation method of 5-methoxytryptamine, the preparation method of described 5-methoxytryptamine comprises the following steps:

[0080] The synthetic route is:

[0081]

[0082] (1) Add 4-methoxyphenylhydrazine hydrochloride (100g, 0.57mol), ethanol (300g), 36% hydrochloric acid (30g , 0.25mol), under stirring, add 4-chlorobutyraldehyde dimethyl acetal (100g, 0.66mol) at one time, raise the temperature to 85°C, react for 10h, TLC shows that the reaction is complete, stop heating, cool down to 60°C, concentrate under reduced pressure Obtain 235g of concentrated solution, the purity of 3-(2-haloethyl)-5-methoxyl-1H-indole in this concentrated solution is 99.0%;

[0083] (2) In a 5L autoclave with stirring and a thermometer, add the concentrated solution (120g) obtained in step (1), ethanol (360g), 28% ammonia water (190g), check that the seal is good, stir evenly, and heat up to 90°C After 10 hours of reaction, heating was...

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Abstract

The invention provides a preparation method of 5-methoxytryptamine. The preparation method of the 5-methoxytryptamine comprises the following steps: (1) in the presence of an acid, carrying out a reaction on 4-methoxyphenylhydrazine salt and 4-halogenated butyraldehyde dimethyl acetal to obtain 3-(2-halogenated ethyl)-5-methoxy-1H-indole; and (2) enabling the 3-(2-halogenated ethyl)-5-methoxy-1H-indole obtained in the step (1) to react with ammonia water, so as to obtain the 5-methoxytryptamine. According to the invention, a total synthesis method in which 4-methoxyphenylhydrazine hydrochloride and 4-chlorobutyraldehyde dimethyl acetal are used as starting materials is adopted, a final product is obtained through steps of cyclization, amination and the like, the whole process flow of the method is simple to operate, and meanwhile, an intermediate obtained in the intermediate step can directly enter the next reaction without refining and drying, so that the method is suitable for industrial production. The method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and pharmacy, and in particular relates to a preparation method of 5-methoxytryptamine. Background technique [0002] 5-Methoxytryptamine is a tryptamine derivative closely related to the neurotransmitters melatonin and serotonin. It acts as a full agonist at 5-HT1, 5-HT2, 5-HT4, 5-HT6 and 5-HT7 receptors, but has no affinity for 5-HT3 receptors. Is a melatonin-related compound. [0003] At present, with the progress of society and the development of science and technology, the use value and application of 5-methoxytryptamine have been widely concerned, but there are different processes for the preparation of 5-methoxytryptamine. [0004] CN110818610A discloses a preparation method of melatonin. The preparation method of described melatonin comprises the steps: (a) phthalimide, 1,3-dichloropropane, sodium iodide and ethyl acetoacetate are reacted under the action of alkali in a solven...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/16
CPCC07D209/16
Inventor 韩振玉张浩郝振杨杰
Owner 阜阳欣奕华制药科技有限公司
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