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Method for synthesizing agmatine sulfate

A technology of agmatine sulfate and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the industrial policy of energy saving and emission reduction, unpleasant smell of alkyl mercaptans, unfavorable Labor protection and other issues, to achieve great implementation value and social and economic benefits, to facilitate industrial production, and to achieve high sample purity

Active Publication Date: 2010-06-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the weak point of this method is: (1) reaction yield is low (about 40%); (2) reaction easily produces " three wastes ", especially the alkyl mercaptan smell that produces is unpleasant, easily pollutes environment, It is not conducive to labor protection, and it is not in line with the industrial policy of energy conservation and emission reduction

Method used

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  • Method for synthesizing agmatine sulfate
  • Method for synthesizing agmatine sulfate
  • Method for synthesizing agmatine sulfate

Examples

Experimental program
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Embodiment 1

[0021] Weigh 3.22g (0.02mol) of 1,4-butylenediamine hydrochloride and 2.00g (0.05mol) of NaOH into a 250mL single-necked bottle, add water (10mL), stir magnetically, and distill under reduced pressure after the solid is dissolved , Collect the distillate at 120°C to obtain 1,4-butanediamine, which is used for the next step. Add 1,4-butanediamine, 3.075 g (0.025 mol) of O-methylisourea sulfate and 20 mL of water obtained in the previous step into a 250 mL three-necked flask, and then react with magnetic stirring in a water bath at 30 ° C. After 1 hour, the solution gradually becomes Turbidity, white insoluble matter is formed, continue to stir the reaction, TLC detects the reaction to the end point (about 3 hours), suction filtration, the filtrate is adjusted to pH1 H-NMR δ ppm (400 MHz, D2O) δ: 1.61 (m, 2H), 2.93 (t, 1H), 3.14 (t, 1H).

Embodiment 2

[0023] Weigh 3.22g (0.02mol) of 1,4-butylenediamine hydrochloride and 2.00g (0.05mol) of NaOH into a 250mL single-necked bottle, add water (10mL), stir magnetically, and distill under reduced pressure after the solid is dissolved , Collect the distillate at 120°C to obtain 1,4-butanediamine, which is used for the next reaction. Add 1,4-butanediamine, 3.075g (0.025mol) of O-methylisourea sulfate and 20mL of ethanol obtained in the previous step into a 250mL three-necked flask, and then react with magnetic stirring in a water bath at 30°C. After 2 hours, the solution gradually becomes Turbidity, white insoluble matter is generated, continue to stir the reaction, TLC detects the reaction to the end point (about 4 hours), suction filtration, the filtrate is adjusted to pH<7 with 25% sulfuric acid / ethanol solution, and concentrated under reduced pressure to a viscous transparent oil. Add water (4mL)-ethanol (6mL) for purification, crystallize at 0°C for 4 hours, filter with suction...

Embodiment 3

[0025] Weigh 3.22g (0.02mol) of 1,4-butylenediamine hydrochloride and 2.00g (0.05mol) of NaOH into a 250mL single-necked bottle, add water (10mL), stir magnetically, and distill under reduced pressure after the solid is dissolved , Collect the distillate at 120°C to obtain 1,4-butanediamine, which is used for the next reaction. Add 1,4-butanediamine, 3.075 g (0.025 mol) of O-methylisourea sulfate and 15 mL of water obtained in the previous step into a 250 mL three-necked flask, and then react with magnetic stirring in a water bath at 30 ° C. After 1 hour, the solution gradually becomes Turbidity, white insoluble matter is generated, continue to stir the reaction, TLC detects the reaction to the end point (about 4 hours), suction filtration, the filtrate is adjusted to pH<7 with 25% sulfuric acid / ethanol solution, and concentrated under reduced pressure to a viscous transparent oil. Add water (4mL)-ethanol (6mL) for purification, crystallize at 0°C for 4 hours, filter with suct...

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Abstract

The invention discloses a method for synthesizing agmatine sulfate. The method comprises the following steps of: in a reaction solvent, performing a condensation reaction of 1,4-butanediamine and O-methylisourea sulfate at the temperature of between 20 DEG C below zero and 100 DEG C, utilizing the TLC to detect if the reaction is finished, filtering the reaction solution under vacuum, adding alcoholic solution of sulfuric acid into the obtained filtrate dropwise, adjusting a pH value of the filtrate to below 7, condensing the filtrate to dryness, and re-crystallizing residues to obtain the agmatine sulfate, wherein the reaction solvent is water or a C1 to C3alcohol, the adding mol ratio of the 1,4-butanediamine and the O-methylisourea sulfate is 1:1-1:2.0, and the volume dosage of the reaction solvent is 4 to 20ml / g based on the mass of the O-methylisourea sulfate. The method has the advantages of easy and safe operation, high reaction yield, low production cost, basically no emissionof three wastes, and bigger application values and social economic benefits.

Description

(1) Technical field [0001] The invention relates to a synthetic method of agmatine sulfate. (2) Background technology [0002] Agmatine sulfate (III), also known as 1-(4-aminobutyl)guanidine sulfate, the English name is Agmatine sulfate. [0003] [0004] Agmatine is the product of arginine decarboxylation catalyzed by L-arginine decarboxylase (L-ADC). It is a neurotransmitter and is distributed in most organs and tissues of mammals. organ specificity. Research data show that agmatine has biological activities such as lowering blood sugar, lowering blood pressure, diuresis, anti-inflammation, anti-depression, and inhibiting cell proliferation, especially for N-methyl-D-aspartate (NMDA) receptors. The antagonism is strong and long-lasting, and it has a withdrawal effect on morphine dependence in animals. It is a kind of detoxification drug with great development value. As a medicinal sulfate of agmatine, agmatine sulfate has a bright market application prospect. [000...

Claims

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Application Information

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IPC IPC(8): C07C279/12C07C277/08
Inventor 单伟光叶珊珊王建伟占扎君唐岚侯晓容于海宁
Owner ZHEJIANG UNIV OF TECH
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