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Method for synthesizing 3-amino-1-adamantanol

A technology of adamantanol and a synthesis method, which is applied to the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of difficult industrialization, low safety factor of sodium azide, etc., and achieves simple and easy operation. , The effect of easy availability of raw materials and high yield

Inactive Publication Date: 2010-06-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses sodium azide to react with a low safety factor and is not easy for industrialization

Method used

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  • Method for synthesizing 3-amino-1-adamantanol
  • Method for synthesizing 3-amino-1-adamantanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Take 100mL of dried liquid bromine (dried with concentrated sulfuric acid) and 60g of anhydrous aluminum trichloride in a 250mL three-necked flask, set up a mechanical stirring and reflux condensation device (use saturated sodium bicarbonate solution for tail gas absorption), and place in anhydrous In the state, the temperature was lowered to -20°C, and 30 g of dry adamantanecarboxylic acid powder was quantitatively added within 4 hours under stirring, and reacted at -20°C for 48 hours, and then reacted at 20°C for 5 hours to stop the reaction.

[0024] Pour the reacted product into a large beaker containing 500g of crushed ice and 300mL of dichloromethane to cool, add sodium bisulfite solution under stirring to remove excess liquid bromine, extract and separate the organic phase, and then add 250mL of 1mol / L Stir the sodium hydroxide solution in the organic phase, extract and separate the lye layer, then acidify it with 2mol / L hydrochloric acid until it becomes acidic, ...

Embodiment 2

[0030] Take 50mL of dried liquid bromine (dried with concentrated sulfuric acid) and 10g of anhydrous aluminum chloride in a 150mL three-necked flask, set up a mechanical stirring and reflux condensation device (use saturated sodium bicarbonate solution for tail gas absorption), and place in anhydrous state Cool down to -10°C, slowly add dry 18g adamantanecarboxylic acid powder within 4 hours under stirring, react at -10°C for 50 hours, then react at 25°C for 5 hours, and stop the reaction.

[0031] Pour the obtained product into a large beaker containing crushed ice to cool, add sodium bisulfite solution under stirring to remove excess liquid bromine, then pour into 200mL dichloromethane solvent, extract and separate the organic phase, and then add 100mL1mol / L hydroxide Stir the sodium solution in the organic phase, extract and separate the lye layer, then acidify it with 2mol / L hydrochloric acid until it becomes acidic, let it stand still, precipitate out, filter and dry. Re...

Embodiment 3

[0037]Take 100mL of dried liquid bromine (dried with concentrated sulfuric acid) and 40g of anhydrous aluminum trichloride in a 250mL three-necked flask, set up a mechanical stirring and reflux condensation device (use saturated sodium bicarbonate solution for tail gas absorption), and place in anhydrous In the state, the temperature was lowered to 0°C, and 25g of dry adamantanecarboxylic acid powder was quantitatively added within 4 hours under stirring, and reacted at 0°C for 55 hours, then reacted at 30°C for 5 hours, and stopped the reaction.

[0038] Pour the reacted product into a large beaker containing 500g of crushed ice and 300mL of dichloromethane to cool, add sodium bisulfite solution under stirring to remove excess liquid bromine, extract and separate the organic phase, and then add 250mL of 1mol / L Stir the sodium hydroxide solution in the organic phase, extract and separate the lye layer, then acidify it with 2mol / L hydrochloric acid until it becomes acidic, let i...

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Abstract

The invention discloses a method for synthesizing 3-amino-1-adamantanol. The structural formula of the 3-amino-1-adamantanol is as follows. Using adamantanecarboxylic acid as starting material, the method synthesizes the 3-amino-1-adamantanol according to the following reaction steps: bromate 3-amino-1-adamantanol is synthesized by way of bromination, modified curtius rearrangement and hydrolyzation, and finally, bromate is removed by a alkaline liquor treatment method, so that the 3-amino-1-adamantanol is obtained. The invention has the advantages of simple and easy operation, available materials, less reaction steps and high product yield.

Description

technical field [0001] The invention relates to a synthesis method of 3-amino-1-adamantanol. Background technique [0002] Adamantane (tricyclo[3.3.1.1 [37] ] decane, molecular formula C 10 h 16 ) is a ring-shaped tetrahedral hydrocarbon with a highly symmetrical molecular structure, similar to a diamond lattice unit, close to a spherical hydrocarbon molecule, and has unique physical and chemical properties. Adamantane and its derivatives are widely used in many fields such as biomedicine, functional polymer materials, lubricants, catalysts, surfactants, pesticides, etc., and are called a new generation of fine chemical raw materials. Its unique structure makes it have excellent fat solubility and low toxicity, and exhibits unique pharmacological effects. Adamantane and its derivatives can be used in medicine to manufacture various specific drugs. For example, adamantane derivatives are used in the synthesis of specific drugs (prevention and treatment against influenza v...

Claims

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Application Information

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IPC IPC(8): C07C215/44C07C213/08
Inventor 郭建维谢炳玉刘卅陈旭东刘鸿
Owner GUANGDONG UNIV OF TECH
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