Synthesis method for deuterium marked ractopamine

A technique for ractopamine and a synthetic method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxyl compounds, etc., can solve problems such as severe reaction conditions and cumbersome reaction routes, achieve simple synthesis steps, reduce production costs, The effect of temperature control

Inactive Publication Date: 2015-01-28
SHANGHAI INST OF MEASUREMENT & TESTING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction route of this method is relatively cumbersome and the reaction conditions are relatively severe.

Method used

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  • Synthesis method for deuterium marked ractopamine
  • Synthesis method for deuterium marked ractopamine
  • Synthesis method for deuterium marked ractopamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) The synthetic method of deuterium-labeled raspberry ketone

[0027]

[0028] In a 100mL three-necked flask equipped with a stirrer and a thermometer, add deuterium-labeled acetone (5.77g, 90mmol), sodium hydroxide (0.8g, 20mmol), and 3.5mL of distilled water. Formaldehyde solution (among them, p-hydroxybenzaldehyde (7.33g, 60mmol), sodium hydroxide (2.44g, 61mmol), distilled water 57.5mL), the temperature was controlled at 30°C, the addition was completed in 20min, and the stirring reaction was continued for 3h; Neutralize to pH=5~6, add activated carbon for decolorization, and filter. After the filtrate was cooled and crystallized, the filter cake was filtered and dried to obtain a deuterium-labeled unsaturated ketone (7.88 g, 79%).

[0029] Put deuterium-labeled unsaturated ketone (3.0g, 18mmol), absolute ethanol 174mL, and Raney Ni 1g into a stainless steel autoclave, and pass H 2 (1MPa). After stirring at 70-80° C. for 2 h, the reaction solution was filter...

Embodiment 2

[0045] (1) The synthetic method of phenyl ring deuterium label raspberry ketone

[0046]

[0047] In a 100mL three-necked flask equipped with a stirrer and a thermometer, add acetone (7.9mL, 108mmol), sodium hydroxide (0.8g, 20mmol), and 3.5mL of distilled water. After stirring evenly, slowly add deuterium-labeled p-hydroxybenzene Formaldehyde solution (deuterium-labeled p-hydroxybenzaldehyde (7.56g, 60mmol), sodium hydroxide (2.44g, 61mmol), distilled water 57.5mL), the temperature was controlled at 30°C, the addition was completed in 20min, and the stirring was continued for 3h. After the reaction, neutralize with mineral acid to pH=5-6, add active carbon for decolorization, and filter. After the filtrate was cooled and crystallized, the filter cake was filtered out and dried to obtain a deuterium-labeled unsaturated ketone (8.4 g, 83%).

[0048] Put deuterium-labeled unsaturated ketone (3.0g, 18mmol), absolute ethanol 174mL, and Raney Ni 1g into a stainless steel autocl...

Embodiment 3

[0054] (1) The synthetic method of deuterium-labeled raspberry ketone is the same as in Example 1.

[0055] (2) The synthesis method of deuterium-labeled 1-methyl-3-(4-hydroxyphenyl)-propylamine hydrochloride is the same as in Example 1.

[0056] (3) The synthetic method of deuterium-labeled acetophenone amines intermediate

[0057]

[0058] Add 1-methyl-3-(4-hydroxyphenyl)-propylamine hydrochloride (5.3g, 32mmol), deuterium-labeled ω-bromo-p-hydroxyacetophenone (5.4g, 25mmol) into a 250mL three-necked flask, Sodium carbonate (3.4g, 32mmol), ethyl acetate 30mL and saturated sodium carbonate aqueous solution 50mL, after mechanically stirring rapidly for 2.5h, add deuterium-labeled ω-bromo-p-hydroxyacetophenone (1.3g, 6mmol) in ethyl acetate solution 10mL , Continue to react at 60°C for 2h. Filter, transfer the filter cake to a 50mL flask, add 19mL of concentrated hydrochloric acid and 19mL of water, and reflux for 30min. After cooling, filter and wash the filter cake with...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method for ractopamine marked by stable isotope deuterium. The method comprises the steps of firstly, carrying out aldol reaction on deuterium marked or non-marked p-hydroxy benzaldehyde and deuterium marked or non-marked acetone so as to generate deuterium marked raspberry ketone, then carrying out reductive amination, carrying out nucleophilic substitution reaction on deuterium marked or non-marked Omega-bromine-hydroxyacetophenone, reducing so as to prepare the deuterium marked ractopamine. The synthesis method has simple and efficient steps, the synthesized deuterium marked ractopamine has the purity of more than 99%, and the mark point isotope abundance is greater than 99%. Furthermore, the synthesis method has high finished product yield and high product yield, and effectively lowers the production cost. The deuterium marked ractopamine prepared by the synthesis method can be used for detection of residue of forbidden veterinary drug in food safety field and research of metabolic mechanism of ractopamine.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for synthesizing ractopamine labeled with stable isotope deuterium. Background technique [0002] Ractopamine is a synthetic β-adrenergic receptor agonist, which can be used to treat congestive heart failure, muscular dystrophy, increase muscle and reduce fat accumulation. It is used as a new type of clenbuterol by some pig farms use. However, in animal experiments, it was found that it has certain toxicity, the median lethal dose for mice is 3547-2545 mg / kg, and the median lethal dose for rats is 474-365 mg / kg. When the human body eats a large amount of meat or offal containing ractopamine residues, it may cause symptoms of poisoning, such as dyspnea, nausea, vomiting, dizziness, headache, muscle tremors, heart palpitations, arrhythmia, blood pressure rise, promote cardiovascular disease, affect reproduction system etc. Therefore, in 2014, the Ministry of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/60C07C213/08
Inventor 李杰许卓妮于瑞祥陈鹰王虎
Owner SHANGHAI INST OF MEASUREMENT & TESTING TECH
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