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A kind of synthetic method of arecoline

A synthesis method and technology of arecoline are applied in the field of synthesis of arecoline, can solve the problems of high toxicity of methyl iodide, low single-step yield and high price, and achieve the effects of simple preparation method, high product purity and high yield

Active Publication Date: 2022-07-08
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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  • A kind of synthetic method of arecoline
  • A kind of synthetic method of arecoline
  • A kind of 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 under reflux for 5 hours, cool down to 20-30°C after completion, add 15g formic acid dropwise , 1.5 hours of dropwise addition, stirring for half an hour, suction filtration (precipitated impurities, such as sodium formate), washing the filter cake to obtain the methanol solution of M1.

[0036] 2) Synthesis of M2

[0037]

[0038] M1 methanol solution, 28 g methylamine methanol solution (30 wt %) and 0.4 g KI were added to the reaction flask, and the reaction was carried out at 35-45° C. for 7.5 h. After the reaction was completed, the temperature was lowered to 10-20°C, 15ml of water was added, extracted with dichloromethane, washed with 15ml of 10% dilute hydrochloric acid, washed with 15ml of saturated brine, distilled under reduced pressure with dichloromethane to dryness to obtain ...

Embodiment 2

[0046] 1) Synthesis of M1

[0047] Add 50g (0.299mol) methyl 3-bromopropionate, 74g sodium methoxide methanol solution (30wt%), 150ml methanol into the reaction flask, heat under reflux for 6 hours, cool down to 20-30°C after completion, add 15g formic acid dropwise, The dropwise addition was completed in 1 hour, and 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] M1 methanol solution, 28 g methylamine methanol solution (30 wt %), 0.4 g KI were added to the reaction flask, and the reaction was carried out at 35-45° C. for 7 h. After the reaction was completed, the temperature was lowered to 10-20° C., 15 ml of quantitative water was added, extracted with dichloromethane, washed with 15 ml of 10% dilute hydrochloric acid solution, washed with saturated brine, and distilled to dryness with dichloromethane to obtain 38.7 g of compound M2, yield: 75.59%; Pu...

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Abstract

The invention discloses a synthesis method of arecoline. The synthesis method uses methyl 3-bromopropionate as a starting material, and sequentially undergoes condensation with sodium methoxide clesen ester, ring closure with methylamine, reduction with sodium borohydride and dehydration under alkaline conditions to obtain arecoline. The present invention uses methyl 3-bromopropionate and methylamine alcohol solution as raw materials, avoids the use of high-cost methyl iodide or highly toxic dimethyl sulfate in the N methylation step, and controls safety problems from the source.

Description

technical field [0001] The invention relates to a method for synthesizing arecoline, and belongs to the technical field of organic synthesis. Background technique [0002] Arecoline, chemically called methyl 1,2,5,6-tetrahydro-1-methyl-3-picolinate, is a compound with great medicinal value. Arecoline is a cholinergic drug that can make pupils narrow and reduce intraocular pressure, and can be used to treat glaucoma. Arecoline has a strong paralyzing effect on tapeworm muscles, making the worms lose their ability to adhere 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 digestive glands, which is beneficial to paralyzing the worms. rapid elimination of the body. [0003] U.S. Patent US2506458A has introduced the synthetic method of arecoline, the method takes 3,3-iminodipropionitrile as raw material, undergoes methylation, hydrolysis, ester condensati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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