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Chemical synthesis method of piperine

A technology of chemical synthesis and piperine, which is applied in the field of medicine and chemical industry, can solve the problems of rising product prices and product output that cannot meet the needs of the market, and achieve the effects of cheap price, easy large-scale industrial production, and increased yield

Inactive Publication Date: 2013-12-11
天津市利发隆化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, with the increasing market demand for piperine, the output of the product cannot meet the demand of the market, and the price of the product has been rising year by year

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of chemical synthesis method of piperine, its step is as follows:

[0031] (1) Preparation of bromopipercycline:

[0032] Dissolve 30g of piperonylcycline in 100ml of glacial acetic acid, slowly add 40g of bromine dropwise within 1 hour at 0°C, keep the reaction temperature at 0°C, after dropping, continue to react for 2h, wash with water twice until neutral, and dry to obtain the product Bromopipercycline 38.7g, yield 78.2%, spare;

[0033] (2) Preparation of α-p-toluenesulfonylfurylhydrazone:

[0034] Dissolve 42g of furfural in 1000ml of anhydrous methanol, then add 78g of p-toluenesulfonyl hydrazide to form a light yellow solution. After reacting at room temperature for 2 hours, pour the reaction solution into ice water and place it in the refrigerator for 1 hour to precipitate a yellow solid. After suction filtration and drying at 100°C, 103 g of α-p-toluenesulfonylfurylhydrazone was obtained with a yield of 92.3%, which was set aside;

[0035] (3) Prepar...

Embodiment 2

[0044] A kind of chemical synthesis method of piperine, its step is as follows:

[0045](1) Preparation of bromopipercycline:

[0046] Dissolve 25g of piperonylcycline in 100ml of formic acid, slowly add 33.3g of bromine dropwise within 1h at -5°C, keep the reaction temperature at -5°C, after dropping, continue to react for 2h, wash with water twice until neutral, and dry to obtain Product bromopipercycline 31.1g, yield 75.5%, set aside;

[0047] (2) Preparation of α-p-toluenesulfonylfurylhydrazone:

[0048] Dissolve 42g of furfural in 1000ml of absolute ethanol, then add 78g of p-toluenesulfonyl hydrazide to form a light yellow solution. After reacting at room temperature for 2 hours, pour the reaction solution into ice water and place it in the refrigerator for 1 hour to precipitate a yellow solid. After suction filtration and drying at 100°C, 100 g of α-p-toluenesulfonylfurylhydrazone was obtained with a yield of 86.6%, which was set aside;

[0049] (3) Preparation of pi...

Embodiment 3

[0058] A kind of chemical synthesis method of piperine, its step is as follows:

[0059] (1) Preparation of bromopipercycline:

[0060] Dissolve 35g of piperonylcycline in 100ml of glacial acetic acid, slowly add 46.5g of bromine dropwise within 1 hour at 10°C, and keep the reaction temperature at 10°C. Product bromopipercycline 45.2g, yield 78.4%, standby;

[0061] (2) Preparation of α-p-toluenesulfonylfurylhydrazone:

[0062] Dissolve 45g of furfural in 1000ml of anhydrous methanol, and then add 82g of p-toluenesulfonylhydrazide to form a light yellow solution. After reacting at room temperature for 2 hours, pour the reaction solution into ice water and place it in the refrigerator for 1 hour to precipitate a yellow solid. After suction filtration and drying at 100°C, 114.5 g of α-p-toluenesulfonylfurylhydrazone was obtained, with a yield of 92.5%, which was set aside;

[0063] (3) Preparation of piperonyl-α-dienal:

[0064] Add 32.3 g of bromopipercycline obtained in st...

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Abstract

The invention relates to a chemical synthesis method of piperine, which comprises the following steps: (1) preparation of bromopiperidine; (2) preparation of alpha-p-tolylsulfonylfuran hydrazone; (3) preparation of piperidinyl-alpha-diolefine aldehyde; (4) preparation of piperidinyl-alpha-diolefine acid; and (5) preparation of piperine.In the invention, the piperidine and bromine react to generate the bromopiperidine, so the bromation selectivity is high; and the bromine mainly goes to the beta position of the piperidine, the yield can reach more than 78%, and the byproducts are fewer. The raw materials, including piperidine, bromine, furfural, p-toluenesulfonhydrazide, piperidine and the like are common raw materials in the market, and are easy to purchase and low in price, so that the raw material cost for producing the piperine is much lower than that of other methods.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, in particular to a chemical synthesis method of piperine. Background technique [0002] Piperine belongs to cinnamon phthaloamide alkaloids and has many clinical effects: antibacterial, anti-inflammatory, treatment of gastrointestinal diseases, rheumatoid arthritis, bruises and neuropathic analgesia. High-purity piperine analgesic injection has a significant pain-reducing effect on severe pain caused by large-scale trauma and advanced cancer, so it can be used for adjuvant treatment of tumors. As a broad-spectrum anticonvulsant, piperine is also widely used in detoxification. It has been tested to have a powerful detoxifying effect on almost all drug addictions. At home and abroad, especially in Southeast Asia, it has been widely used in the clinical treatment of drug addiction. In addition, piperine is also widely used as an additive in modern pharmaceuticals, perfumes, cosmetics...

Claims

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Application Information

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IPC IPC(8): C07D317/60
Inventor 李建发全志利
Owner 天津市利发隆化工科技有限公司
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