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Preparation method of melatonin

A technology of melatonin and compounds, applied in the field of preparation of melatonin, can solve the problems of cumbersome steps, high risk and cost, reagent toxicity, etc., and achieve simple operation, shortened reaction steps and time, and high overall yield Effect

Active Publication Date: 2020-02-21
浙江财和生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a preparation method of melatonin, so as to solve the problems in the prior art that the reagents are highly toxic, dangerous and costly, and the steps are cumbersome

Method used

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  • Preparation method of melatonin

Examples

Experimental program
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Effect test

Embodiment 1

[0049]

[0050] The preparation route of melatonin provided in this embodiment is as shown above, and the preparation method comprises the following steps:

[0051] (1) Add 500 mL of acetonitrile, 100 g of phthalimide and 281.8 g of potassium carbonate to the reaction vessel, stir at room temperature for 30 min, then add 115.19 g of 1,3-dichloropropane and 152.82 g of sodium iodide; After the feeding is completed, gradually raise the temperature to 58-60°C and stir the reaction for 5.5 hours in this temperature range, and take samples to monitor the complete reaction of the raw material phthalimide;

[0052] Then 132.68 g of ethyl acetoacetate was weighed, and slowly added dropwise to the above reaction solution. After the addition, the reaction was continued for 7 h; was 96.2%.

[0053] (2) Add 100mL of water and 121g of p-methoxyaniline to the reaction vessel, cool down to 0-5°C; slowly add 298.53g of concentrated hydrochloric acid (36wt%) to it, and stir for 30min after...

Embodiment 2

[0060] The present embodiment refers to the preparation method of Example 1, the difference is only that step (1) is as follows:

[0061] Add 500mL acetonitrile, 100g phthalimide and 216.1g sodium carbonate to the reaction vessel, stir at room temperature for 30min, then add 115.19g of 1,3-dichloropropane and 152.82g sodium iodide; Gradually raise the temperature to 58-60°C and stir in this temperature range for 5.5 hours, take a sample to monitor the complete reaction of the raw material phthalimide;

[0062] Then 132.68 g of ethyl acetoacetate was weighed, and slowly added dropwise to the above reaction solution. After the addition, the reaction was continued for 7 h; was 90.7%.

Embodiment 3

[0064] The present embodiment refers to the preparation method of Example 1, the difference is only that step (1) is as follows:

[0065] Add 1000mL acetonitrile, 100g phthalimide and 375.7g potassium carbonate to the reaction vessel, stir at room temperature for 30min, then add 153.6g of 1,3-dichloropropane and 203.8g sodium iodide; Gradually raise the temperature to 58-60°C and stir in this temperature range for 5.5 hours, take a sample to monitor the complete reaction of the raw material phthalimide;

[0066] Then 176.9 g of ethyl acetoacetate was weighed and slowly added dropwise to the above reaction solution. After the addition was complete, the reaction was continued for 7 h; was 94.8%.

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Abstract

The invention relates to the technical field of chemical synthesis of medicines, in particular to a preparation method of melatonin. The preparation method of the melatonin comprises the following steps: (a) subjecting phthalimide, 1,3-dichloropropane, sodium iodide and ethyl acetoacetate to a reaction in a solvent under the action of alkali to obtain a compound I; (b) performing a ring closing reaction on the compound I and p-methoxyphenyl diazonium salt in the presence of alkali and a solvent to obtain a compound II; (c) hydrolyzing the compound II under an alkaline condition, and carrying out decarboxylating under an acidic condition to obtain a compound III; and (d) carrying out an acetylation reaction on the compound III to obtain melatonin. According to the preparation method, phthalimide, 1,3-dichloropropane, ethyl acetoacetate and the like are used as raw materials, and the price of the raw materials is low; the intermediate compound I can be obtained through a one-step method,so reaction steps and time are shortened; moreover, the conditions of each reaction step are relatively mild, the raw materials are easy to obtain, and high yield can be obtained.

Description

technical field [0001] The invention relates to the technical field of medicinal chemical synthesis, in particular to a preparation method of melatonin. Background technique [0002] Melatonin, also known as melatonin, its chemical name is 5-methoxy-N-acetyltryptamine (N-(2-(5-methoxy-1H-indol-3-yl)ethyl)acetamide), is An indole compound. Melatonin has a wide range of physiological and pharmacological activities. Its main function is to regulate circadian rhythm, sleep-wake biological rhythm phase transition, improve sleep, and also has anti-oxidation, free radical scavenging, anti-inflammation, anti-apoptosis, lower body temperature, and tumor inhibition. Growth, inhibition of reproductive system function, improvement of memory, treatment of dementia, anti-aging, anti-anxiety, improvement of morphine withdrawal symptoms, improvement of osteoporosis, anti-epilepsy and other functions. In the eye, melatonin is involved in the regulation of circadian rhythm changes in retina...

Claims

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Application Information

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IPC IPC(8): C07D209/14C07D209/48
CPCC07D209/14C07D209/48
Inventor 王明江世坤薛凌霄张文
Owner 浙江财和生物科技有限公司
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