Synthesis method of rimantadine Schiff base

A technology for the synthesis of rimantadine Schiff base, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of long time, many synthesis steps of rimantadine, non-environmental protection, etc. Achieve the effects of less by-products, synergistic catalytic activity, and less dosage

Inactive Publication Date: 2019-01-01
赵旭萌
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthetic steps of this rimantadine are many

Method used

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  • Synthesis method of rimantadine Schiff base
  • Synthesis method of rimantadine Schiff base

Examples

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Embodiment 1

[0022] A method for synthesizing rimantadine Schiff base, comprising preparation of adamantanecarbonyl chloride, preparation of adamantane methyl ketone, preparation of 1-adamantyl methyl ketone oxime, preparation of rimantadine, preparation of rimantadine Schiff base, specifically Steps include:

[0023] Preparation of adamantanecarboxylic acid chloride: Add 1.8g of adamantanecarboxylic acid and 3.6mL of thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, and then add 5mL×2 of benzene for extraction. Gained extract is directly used for next step reaction;

[0024] Preparation of adamantanemethyl ketone: Add 0.10g trimethylaluminum and 0.01g cerium formate to a three-necked flask, then add a benzene solution of adamantanecarbonyl chloride dropwise at 0.25mL / min to make adamantanecarbonyl chloride and trimethylaluminum The reaction produces adamantane methyl ketone. After the reaction is completed, the ...

Embodiment 2

[0029] A method for synthesizing rimantadine Schiff base, comprising preparation of adamantanecarbonyl chloride, preparation of adamantane methyl ketone, preparation of 1-adamantyl methyl ketone oxime, preparation of rimantadine, preparation of rimantadine Schiff base, specifically Steps include:

[0030] Preparation of adamantanecarboxylic acid chloride: Add adamantanecarboxylic acid and thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, then add benzene for extraction, and the obtained extract is directly used in the following one step reaction;

[0031]Preparation of adamantane methyl ketone: Add trimethylaluminum and cerium formate to a three-necked flask, and then drop a benzene solution of adamantanecarbonyl chloride at 0.1mL / min to react adamantanecarbonyl chloride and trimethylaluminum to form adamantane Methyl ketone, after the reaction is completed, pour the reaction solution into ice water ...

Embodiment 3

[0036] A method for synthesizing rimantadine Schiff base, comprising preparation of adamantanecarbonyl chloride, preparation of adamantane methyl ketone, preparation of 1-adamantyl methyl ketone oxime, preparation of rimantadine, preparation of rimantadine Schiff base, specifically Steps include:

[0037] Preparation of adamantanecarboxylic acid chloride: Add adamantanecarboxylic acid and thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, then add benzene for extraction, and the obtained extract is directly used in the following one step reaction;

[0038] Preparation of adamantane methyl ketone: Add trimethylaluminum and cerium formate to a three-necked flask, and then drop a benzene solution of adamantanecarbonyl chloride at 0.5mL / min to react adamantanecarbonyl chloride and trimethylaluminum to form adamantane Methyl ketone, after the reaction is completed, pour the reaction solution into ice water...

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Abstract

The invention discloses a synthesis method of rimantadine Schiff base. The synthesis method comprises the following steps: preparation of adamantane formyl chloride, preparation of adamantane methyl ketone, preparation of 1-adamantane methyl ketoxime, preparation of rimantadine and preparation of rimantadine Schiff base, wherein the preparation of adamantane methyl ketone comprises the following steps: adding trimethylaluminum and cerium formate into a flask; dropwise adding a benzene solution of adamantane formyl chloride so that the adamantane formyl chloride reacts with the trimethylaluminum to generate adamantane methyl ketone; after the reacting, pouring the reaction liquid into ice water, then filtering and drying to obtain light yellow precipitate which is adamantane methyl ketone.The synthesis method disclosed by the invention has the following beneficial effects: the reaction route changes the route of synthesizing adamantane methyl ketone before; by adopting cerium formate to assist in the trimethylaluminum reaction, the reaction conditions are mild, and few byproducts are generated. The synthesis method disclosed by the invention has the advantages of mild conditions, simple and feasible technology, small dosage of catalyst, environmental friendliness and high product yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of rimantadine Schiff base. Background technique [0002] Rimantadine, an amino derivative of saturated tricyclodecane, chemically named α-methyltricyclo[3,3,1,1]decane-1-methylamine, has antiviral and sedative effects, and is used in clinical It is also used to treat sudden severe pain and measles, and it is characterized by fast absorption and small side effects. Amantadine was developed by Bristol Myers Squibb Company of the United States, and was first launched in France in 1987. In 1993, the US FDA approved it for the prevention and treatment of influenza A virus infection, and its clinical efficacy is better than that of amantadine. The mechanism of action of rimantadine is to change the surface charge of the host cell, inhibit the process of the virus penetrating into sensitive cells and releasing nucleic acid, and inhibit the proliferation of...

Claims

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Application Information

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IPC IPC(8): C07C249/02C07C251/16
CPCC07C249/02C07C45/455C07C51/60C07C209/40C07C249/08C07C2603/74C07C251/16C07C61/135C07C49/323C07C251/42C07C211/19
Inventor 赵旭萌
Owner 赵旭萌
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