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A kind of preparation method of 1-amidoadamantane

A technology of adamantane and adamantane, which is applied in the field of preparation of 1-amidoadamantane, can solve the problems of unfavorable industrial production and environmental protection, complex post-processing, low yield, etc., and achieves environmental protection, simple post-processing, The effect that is conducive to industrial production

Inactive Publication Date: 2016-05-25
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by the present invention is to provide a The preparation method of 1-amidoadamantane

Method used

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  • A kind of preparation method of 1-amidoadamantane
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  • A kind of preparation method of 1-amidoadamantane

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Embodiment 1

[0035] Embodiment 1 prepares 1-acetamidoadamantane

[0036] Add 120ml (184g, 1.62mol) of trifluoroacetic acid and 6g (0.0441mol) of adamantane into a 250ml three-necked reaction flask equipped with a stirrer and a thermometer, and place the reaction flask under an ice-water bath to stir, so that the solution temperature drops to 10°C , then add 1.2g (0.0174mol) sodium nitrite, gradually warm up to 25°C within 40min, reddish-brown gas appears in the reaction system, the solid gradually dissolves, continue to react at 25°C for 4h, then add 7.2g (0.176mol) to the reaction solution mol) acetonitrile, heated to reflux at 80°C, reacted for 12 hours, cooled to 25°C, added the reaction solution dropwise into a 500ml reaction bottle containing 360ml water, extracted three times with dichloromethane (100ml each time), combined the extraction The solution was washed with saturated brine and saturated aqueous sodium bicarbonate solution (100ml each), dried over magnesium sulfate with wate...

Embodiment 2

[0037] Embodiment 2 prepares 1-acetamidoadamantane

[0038] Add 60ml (92g, 0.81mol) of trifluoroacetic acid and 6g (0.0441mol) of adamantane into a 100ml three-necked reaction flask equipped with a stirrer and a thermometer, place the reaction flask under an ice-water bath and stir, and lower the temperature of the solution to 10°C , then add 1.2g (0.0174mol) sodium nitrite, gradually warm up to 25°C within 40min, reddish-brown gas appears in the reaction system, the solid gradually dissolves, continue to react at 25°C for 4h, then add 7.2g (0.176mol) to the reaction solution mol) acetonitrile, heated to reflux at 80°C, reacted for 12 hours, cooled to 25°C, added the reaction solution dropwise into a 250ml reaction bottle containing 180ml water, extracted three times with dichloromethane (100ml each time), combined the extraction The solution was washed with saturated brine and saturated aqueous sodium bicarbonate solution (100 ml each), dried over anhydrous magnesium sulfate,...

Embodiment 3

[0039] Embodiment 3 prepares 1-acetamidoadamantane

[0040]Add 120ml (184g, 1.62mol) of trifluoroacetic acid and 6g (0.0441mol) of adamantane into a 250ml three-necked reaction flask equipped with a stirrer and a thermometer, and place the reaction flask under an ice-water bath to stir, so that the solution temperature drops to 10°C , then add 1.2g (0.0174mol) sodium nitrite, gradually warm up to 15°C within 40min, reddish-brown gas appears in the reaction system, the solid gradually dissolves, continue to react at 15°C for 4h, then add 7.2g (0.176mol) to the reaction solution mol) acetonitrile, heated to reflux at 80°C, reacted for 12 hours, cooled to 25°C, added the reaction solution dropwise into a 500ml reaction bottle containing 360ml water, extracted three times with dichloromethane (100ml each time), combined the extraction The solution was washed with saturated brine and saturated aqueous sodium bicarbonate solution (100ml each), dried over magnesium sulfate, filtered ...

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Abstract

The invention discloses a preparation method of 1-amide adamantine. The method comprises the steps that: 1, trifluoroacetic acid is adopted as a solvent, under the existence of oxygen, and under the effect of sodium nitrite, a compound represented by the formula I is subjected to an oxidation reaction, wherein a reaction temperature is 10-35 DEG C; 2, the reaction liquid obtained in the step 1 is mixed with RCN or RCONH2, and a reaction is carried out, such that a compound represented by the formula II is obtained, wherein a reaction temperature is 60-80 DEG C, and R is hydrogen, methyl, ethyl or C3-C5 cycloalkyl. The preparation method provided by the invention has the advantages of mild reaction condition, simple operation, less side product, simple post-treatment, and suitability for industrialized productions. With the method, high-yield and high-purity 1-amide adamantine can be prepared.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of 1-amidoadamantane. Background technique [0002] 1-amidoadamantane is an important intermediate for synthesizing antiviral and Parkinson's syndrome drug amantadine, and their molecular structures are as follows: compounds of formula II and compound of formula IV. Amantadine is the first antiviral drug approved in the United States. Davis first discovered its antiviral effect in 1964, and it was successively included in the British Pharmacopoeia, the US Pharmacopoeia, the Japanese Pharmacopoeia and the Chinese Pharmacopoeia. Domestic production began in 1971. In addition, unilateral amantadine tablets are mainly used to treat Parkinson's disease. [0003] [0004] 1-amido adamantane amantadine [0005] Document JournalofMedicinalChemistry1963, 6 (6), the synthetic method of 760-763 report amantadine, the first step of reaction needs to use aluminum trich...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/02C07C233/03C07C233/06C07C213/10
Inventor 何建勋周后元王宏博姜碧波
Owner SHANGHAI INST OF PHARMA IND CO LTD