Method for preparing 3-amino-1-adamantane alcohol

A technology for amantadine alcohol and amantadine hydrochloride is applied in the preparation of aminohydroxy compounds, the preparation of organic compounds, chemical instruments and methods, etc. The effect of three waste treatment, reducing consumption and reducing cost

Inactive Publication Date: 2010-08-11
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Compare above-mentioned three kinds of synthetic methods, the synthetic raw material of the first method and reaction reagent are easy to get, and cheap, but use a large amount of nitric acid and sulfuric acid in the reaction, three wastes are more, and environmental pollution is serious; Second method fluoboric acid is harmful to human body and The environment is harmful, and TFDO methyl (trifluoromethyl) dioxirane needs to be prepared, which is unstable and expensive; the third method uses 3-acetamidoamantadinol as a raw material and needs to be prepared by itself, and the operation route is long

Method used

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  • Method for preparing 3-amino-1-adamantane alcohol
  • Method for preparing 3-amino-1-adamantane alcohol
  • Method for preparing 3-amino-1-adamantane alcohol

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) 3-nitro-1-adamantanamine

[0027]

[0028] Take 14.0mL (0.21mol) HNO 3 Put it into an ice-water bath, then add 12mL (0.21mol) of sulfuric acid, 21.1g (0.21mol) of potassium nitrate, stir and cool to -5°C, add 20.0g (0.11mol) of amantadine hydrochloride in batches within 30min, and react in an ice-water bath After 1 hour, continue to react at room temperature for 30 hours to obtain a light yellow liquid; then pour it into 100 mL of ice water and continue stirring for 30 minutes to obtain a blue-green liquid;

[0029] (2) 3-Amino-1-adamantanol

[0030]

[0031] Under mechanical stirring, add 48.0 g (0.85 mol) KOH in batches to the blue-green solution prepared in step (1), keep the temperature below 80 ° C, continue stirring for 1 h after the addition, filter with suction, wash with dichloromethane and extract two Next, the organic layer was taken, dried over anhydrous sodium sulfate, and evaporated to dryness with a rotary evaporator to obtain a white solid, w...

Embodiment 2

[0039] (1) 3-nitro-1-adamantanamine

[0040] Take nitric acid 20.0mL (0.28mmol) HNO 3Add it into an ice-water bath, then add 30mL (0.56mmol) of sulfuric acid, add a solution of 23.8g (0.28mol) of sodium nitrate and 40mL of water, stir and cool to -5°C, add 52.4g (0.28mL) of amantadine hydrochloride in batches within 30min mol), after 2 hours of reaction in an ice-water bath, the reaction was continued at room temperature for 30 hours to obtain a light yellow liquid; then poured into 150 mL of ice water and continued to stir for 30 minutes to obtain a blue-green liquid;

[0041] (2) 3-Amino-1-adamantanol

[0042] Under mechanical stirring, add 47.0 g (0.84 mol) KOH in batches to the blue-green solution obtained in (1), keep the temperature below 80 ° C, continue stirring for 1 h after the addition, filter with suction, wash with dichloromethane and extract two Next, the organic layer was taken, dried over anhydrous sodium sulfate, and evaporated to dryness with a rotary evapo...

Embodiment 3

[0044] Potassium nitrate was used to replace sodium nitrate in step (1) of Example 2, and nitration and hydroxylation reactions were carried out to obtain 3-amino-1-adamantanol with a yield of 69%, mp: 266-269°C.

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Abstract

The invention relates to a method for preparing 3-amino-1-adamantane alcohol. The method comprises the following steps of: adding amantadine hydrochloride into a nitrating agent in batches, performing reaction for 1 to 2 hours in an ice-water bath and performing reaction for 1 to 30 hours at room temperature to obtain yellowish liquid; pouring the yellowish liquid into ice, continuously reacting for 0.5 to 2 hours with stirring to obtain blue-green liquid; and adding solid base into solution obtained by the step 2 with stirring, keeping temperature below 80 DEG C, regulating pH to be between 10 and 12, performing reaction for 30 minutes with stirring, leaching, extracting reaction liquid by using dichloromethane, drying the obtained product with anhydrous sodium sulfate, steaming off the dichloromethane and performing recrystallization by using ethyl acetate to obtain white solid. The preparation method has the advantages of readily available starting raw materials, simple reaction operation, short route, environmental friendliness, easy industrial production and good application prospect, and also reduces cost for the synthesis of Vildagliptin serving as a medicament for treatingdiabetes; and the yield of products reaches 75 percent.

Description

technical field [0001] The invention belongs to the field of preparation of adamantanol compounds, in particular to a preparation method of 3-amino-1-adamantanol. Background technique [0002] Amantadine compounds are important pharmaceutical intermediates. At present, there are three main types of adamantane derivatives used clinically at home and abroad, namely amantadine hydrochloride, amantadine hydrochloride, and memantine hydrochloride. It is used as an antiviral agent, has the function of padamine, can treat Parkinson's disease, has anti-influenza virus activity in vitro, and has a remarkable effect in the treatment of cerebrovascular disorders and senile dementia. Depression and cocaine drug dependence treatment have good therapeutic effects. The main component of crack and other antiviral cold medicines is 1-amantadine hydrochloride. The synthesis and pharmaceutical research on various new amantadine derivatives has never stopped. [0003] In recent years, with th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/44C07C213/00
Inventor 赵圣印叶香丽
Owner DONGHUA UNIV
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