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Synthetic method of arecoline

A synthetic method and the technology of arecoline, which are applied in the field of synthesis of arecoline, can solve the problems of low single-step yield, high toxicity of methyl iodide, and high toxicity of dimethyl sulfate, and achieve high yield, simple preparation method, and high-quality products. The effect of high purity

Active Publication Date: 2021-04-23
济南周行医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The methyl iodide used in this synthetic method is highly toxic and expensive, and dimethyl sulfate is highly toxic, and the yield in the reduction step is only about 30%, and the yield in a single step is too low

Method used

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  • Synthetic method of arecoline
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  • Synthetic method of arecoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Synthesis of M1

[0034]

[0035] Add 50g (0.299mol) methyl 3-bromopropionate, 54g methanol solution of sodium methoxide (30wt%) and 150ml methanol to the reaction flask, heat to reflux for 5 hours, cool down to 20-30°C after reaction, add 15g formic acid dropwise After 1.5 hours, the dropwise addition was completed, and after stirring for half an hour, suction filtration (precipitated impurities, such as sodium formate), washing the filter cake, obtained a methanol solution of M1.

[0036] 2) Synthesis of M2

[0037]

[0038] Add M1 methanol solution, 28g methylamine methanol solution (30wt%) and 0.4g KI into the reaction flask, and react at 35-45°C for 7.5h. After the reaction, cool down to 10-20°C, add 15ml of water, extract with dichloromethane, wash with 15ml of 10% dilute hydrochloric acid, wash with 15ml of saturated saline, and distill the dichloromethane to dryness under reduced pressure to obtain 38.4g of compound M2. Yield: 75.01% Purity: 98.22%. ...

Embodiment 2

[0046] 1) Synthesis of M1

[0047] Add 50g (0.299mol) methyl 3-bromopropionate, 74g sodium methoxide methanol solution (30wt%), and 150ml methanol to the reaction flask, and heat to reflux for 6 hours. After 1 hour of dropwise addition, after stirring for half an hour, suction filtration was performed, and the filter cake was washed to obtain a methanol solution of M1.

[0048] 2) Synthesis of M2

[0049] Add M1 methanol solution, 28g methylamine methanol solution (30wt%) into the reaction flask, add 0.4g KI, and react at 35-45°C for 7h. Cool down to 10-20°C after the reaction, add 15ml of quantitative water, extract with dichloromethane, wash with 15ml of 10% dilute hydrochloric acid solution, wash with saturated brine, distill dichloromethane to dryness, and obtain 38.7g of compound M2, yield: 75.59%; purity: 98.16%.

[0050] 3) Synthesis of M3

[0051] Add 35g (0.204mol) of compound M2, 150ml of methanol, and 11.7g of sodium borohydride into the reaction flask for 10 ti...

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PUM

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Abstract

The invention discloses a synthetic method of arecoline. The synthetic method comprises the following steps: taking methyl 3-bromopropionate as an initial raw material, sequentially carrying out sodium methoxide claisen ester condensation, methylamine cyclization, sodium borohydride reduction and dehydration under alkaline conditions to obtain arecoline. According to the method, methyl 3-bromopropionate and a methylamine alcohol solution are used as the raw materials so that the problem that methyl iodide or highly toxic dimethyl sulfate with high cost is used in an N-methylation step, and the safety is controlled from the source is avoided.

Description

technical field [0001] The invention relates to a synthesis method of arecoline, which belongs to the technical field of organic synthesis. Background technique [0002] Arecoline, whose chemical name is 1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester, is a compound with great medicinal value. Arecoline is a cholinomimetic drug, which can make the pupil narrow and reduce the intraocular pressure, and can be used to treat glaucoma. Arecoline has a strong paralyzing effect on the muscles of tapeworms, making the worms lose the ability to cling to the intestinal wall. In addition, the drug has a muscarinic effect on the host, which strengthens intestinal peristalsis and increases the secretion of Chemicalbook from the digestive glands, which is beneficial to the paralysis of tapeworms. rapid elimination of the body. [0003] U.S. Patent US2506458A has introduced the synthetic method of arecoline, and this method is to take 3,3-iminodipropionitrile as raw ma...

Claims

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Application Information

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IPC IPC(8): C07D211/78
CPCC07D211/78Y02P20/584
Inventor 董万荣孙慧娟杨波勇郇利刚张雷雷
Owner 济南周行医药科技有限公司
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