Process for synthesizing trans-4-amino-1-adamantanol hydrochloride

A kind of technology of adamantanol and synthesis process, which is applied in the preparation of amino hydroxyl compounds, the preparation of organic compounds, Raney type catalysts, etc., can solve the problems of expensive, difficult to prepare, and unsuitable for industrial production, and achieve low price and high product quality. The effect of high quality and yield and reduction of production cost

Inactive Publication Date: 2010-06-16
重庆浩康医药化工集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route is ammoniated with 7 moles per liter of ammonia-methanol solution, which is difficult to prepare, expensive, and not suitable for industrial production

Method used

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  • Process for synthesizing trans-4-amino-1-adamantanol hydrochloride
  • Process for synthesizing trans-4-amino-1-adamantanol hydrochloride
  • Process for synthesizing trans-4-amino-1-adamantanol hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthetic route of the present invention is as follows:

[0027]

[0028] Preparation of 5-Hydroxy-2-adamantanone oxime

[0029] 5-Hydroxy-2-adamantanone (15g, 90.2mmol) was dissolved in 100ml of ethanol, 80ml of 1N sodium hydroxide solution of hydroxylamine hydrochloride (10g, 143.9mmol) was added, and the temperature was raised to 100°C for 2 hours. Ethanol was evaporated, water and dichloromethane were added, stirred for 10 minutes, filtered, the solid was collected, the filtrate was separated, the water phase was extracted twice with dichloromethane, the organic phase was combined and the solvent was distilled off, the obtained solid was combined with the filter cake, Ethyl acetate was recrystallized to obtain 5-hydroxy-2-adamantanone oxime (12 g, mass yield 80%).

[0030] Preparation of 4-amino-1 adamantanol

[0031] Add 5-hydroxy-2-adamantanone oxime (10g, 55mmol), 100ml ethanol, 2g Raney nickel into the autoclave, after nitrogen replacement, adjust the h...

Embodiment 2

[0035] Preparation of 5-Hydroxy-2-adamantanone oxime

[0036] 5-Hydroxy-2-adamantanone (15g, 90.2mmol) was dissolved in 100ml of ethanol, 80ml of 1N sodium hydroxide solution of hydroxylamine hydrochloride (10g, 143.9mmol) was added, and the temperature was raised to 100°C for 2 hours. Ethanol was evaporated, water and dichloromethane were added, stirred for 10 minutes, filtered, the solid was collected, the filtrate was separated, the water phase was extracted twice with dichloromethane, the organic phase was combined and the solvent was distilled off, the obtained solid was combined with the filter cake, Ethyl acetate was recrystallized to obtain 5-hydroxy-2-adamantanone oxime (12 g, mass yield 80%).

[0037] Preparation of 4-amino-1 adamantanol

[0038] Add 5-hydroxyl-2-adamantanone oxime (10g, 55mmol), 100ml alcohol solvent in the autoclave, select one or more of ethanol, methanol, isopropanol, n-butanol, tert-butanol, 0.5g of Raney nickel, after nitrogen replacement, ad...

Embodiment 3

[0042] Preparation of 5-Hydroxy-2-adamantanone oxime

[0043]5-Hydroxy-2-adamantanone (15g, 90.2mmol) was dissolved in 100ml of ethanol, 80ml of 1N sodium hydroxide solution of hydroxylamine hydrochloride (10g, 143.9mmol) was added, and the temperature was raised to 100°C for 2 hours. Ethanol was evaporated, water and dichloromethane were added, stirred for 10 minutes, filtered, the solid was collected, the filtrate was separated, the water phase was extracted twice with dichloromethane, the organic phase was combined and the solvent was distilled off, the obtained solid was combined with the filter cake, Ethyl acetate was recrystallized to obtain 5-hydroxy-2-adamantanone oxime (12 g, mass yield 80%).

[0044] Preparation of 4-amino-1 adamantanol

[0045] Add 5-hydroxy-2-adamantanone oxime (10g, 55mmol), 100ml methanol, 5g Raney nickel into the autoclave, after nitrogen replacement, adjust the hydrogen pressure to 5.0MPa, and react at about 0°C for 48 hours. After filtration...

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Abstract

The invention discloses a process for synthesizing trans-4-amino-1-adamantanol hydrochloride, which comprises the steps of taking 5-hydroxy-2-adamantantanone as raw material, oximating by using hydroxylamine hydrochloride, carrying out hydrogenation reduction by using raney nickel for obtaining 4-amino-1-adamantanol, and carrying out three-step reaction of acidification, salt formation and then recrystallization with methanol for obtaining the trans-4-amino-1-adamantanol hydrochloride. Compared with the process reported by the existing patent literature, the process has the advantages of simple operation, easy obtainment of raw materials, low cost, high yield and the like.

Description

technical field [0001] The invention relates to a method for chemically synthesizing medicines, in particular to a synthesis process for trans-type 4-amino-1-adamantanol hydrochloride. Background technique [0002] Trans-4-amino-1-adamantanol hydrochloride, English name: trans-4-Aminoadamantan-1-olhydrochloride. The number of biologically active adamantane semi-family compounds is gradually increasing. Adamantane derivatives have good antiviral effect, can prevent influenza virus, herpes virus infection, have the effect of resisting Parkinson's syndrome, and are applied to the treatment of senile dementia (for example: memantine is used as the first one for the treatment of advanced NMDA antagonists for Alzheimer's disease (AD). In addition, adamantane and its derivatives are widely used in medicine, polymers, surfactants, catalysts, photographic photosensitive materials and other fields, so they are called "new generation fine chemical raw materials". Therefore, the deve...

Claims

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Application Information

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IPC IPC(8): C07C215/44C07C213/08B01J25/02
Inventor 张孝琴李朝亮刘玥
Owner 重庆浩康医药化工集团有限公司
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