Tyramine compound and preparation method thereof

The technology of a compound and tyramine, which is applied in the field of tyramine compound and its preparation, can solve the problems of yield limitation, environmental pollution, difficulty in product purification and the like, and achieves the effects of strong positioning, reduced production cost and low price

Inactive Publication Date: 2016-07-20
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a large amount of organic solvents are used in the reaction process, which will cause great pollution to the environment.
At the same time, due to the use of tyrosine as a raw material, it is difficult to purify the product, and the yield will be limited to a certain extent.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation method of tyramide is characterized in that, comprises the following steps:

[0021] Dissolve phenol in anhydrous ether, add to the reaction kettle, pass through boron trifluoride, add formic acid, keep the temperature at 10°C, continue the reaction for 2 hours, add nitromethane and ammonium acetate, control the temperature to reflux at 110°C After 2 hours, cool down to 0°C to precipitate crystals. After suction filtration and drying, recrystallize in ethanol to obtain compound b. Add compound b and absolute ethanol to the reaction kettle, add TiO 2 -NiO-Fe mixture catalyst, stir, vacuumize and feed hydrogen into the reaction kettle, control the temperature at 50°C, continue the reaction for 4 hours, remove the catalyst by suction filtration, extract with dichloromethane, remove the solvent, and obtain the target product phenol amine. The yield was 69.3%.

Embodiment 2

[0023] The preparation method of tyramide is characterized in that, comprises the following steps:

[0024] Dissolve phenol in anhydrous ether, add to the reaction kettle, pass through boron trifluoride, add formic acid, keep the temperature at 15°C, continue the reaction for 2 hours, add nitromethane and ammonium acetate, control the temperature at 110°C and reflux After 2 hours, cool down to 5°C to precipitate crystals. After suction filtration and drying, recrystallize in ethanol to obtain compound b. Add compound b and absolute ethanol to the reaction kettle, add TiO 2 -NiO-Fe mixture catalyst, stir, vacuumize and feed hydrogen into the reaction kettle, control the temperature at 55 ° C, continue the reaction for 5 hours, remove the catalyst by suction filtration, extract with dichloromethane, remove the solvent, and obtain the target product phenol amine. The yield was 70.7%.

Embodiment 3

[0026] The preparation method of tyramide is characterized in that, comprises the following steps:

[0027] Dissolve phenol in anhydrous ether, add to the reaction kettle, pass through boron trifluoride, add formic acid, keep the temperature at 10°C, continue the reaction for 2 hours, add nitromethane and ammonium acetate, control the temperature to reflux at 110°C After 2 hours, cool down to 5°C to precipitate crystals. After suction filtration and drying, recrystallize in ethanol to obtain compound b. Add compound b and absolute ethanol to the reaction kettle, add TiO 2 -NiO-Fe mixture catalyst, stirred, vacuumized, and hydrogen gas was introduced into the reaction kettle, and the temperature was controlled at 50 ° C. After continuing the reaction for 5 hours, the catalyst was removed by suction filtration, extracted with dichloromethane, and the solvent was removed to obtain the target product phenol amine. The yield was 78.6%.

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PUM

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Abstract

The invention discloses a tyramine compound and a preparation method thereof. The preparation method includes the following steps: after phenol and formic acid first react for 2 hours, nitromethane and ammonium acetate are added, compound b can be obtained by reaction after 2 hours of reflux, hydrogen is then injected into the compound b produced in the reaction under the catalysis of TiO2-NiO-Fe mixture, temperature is controlled at 50DEG C to 60DEG C, and after 4 to 5.5 hours of continuous reaction, the target product, tyramine, is obtained. The materials of the method are cheap and easy to obtain, the synthetic route is novel, the cost is low, operation condition requirement is low, and the preparation method is environment-friendly and suitable for mass industrial production.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to a tyramide compound and a preparation method thereof. Background technique: [0002] Tyramine, also known as p-hydroxyphenylethylamine, is a white or off-white solid. Tyramine, a compound originally isolated from ergot alkaloids and decaying animal tissues, is an important synthetic drug intermediate. It has the effect of raising blood pressure and stimulating the uterus, and it can also be used to treat migraines and diagnose cancer cells. Therefore, people have carried out a lot of research on its synthetic method. [0003] Chinese patent 200910055103.7 discloses a new method for preparing tyramine. Using tyrosine as a raw material, it undergoes a catalytic decarboxylation reaction with a decarboxylation catalyst in an organic solvent to obtain the target product tyramine. The simplified reaction steps and novel synthesis route of the invention make the operating condit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C215/52
CPCC07C221/00C07C213/08C07C225/16C07C215/52
Inventor 叶芳
Owner 叶芳
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