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Method for synthesizing amantadine

A technology for amantadine and adamantane, which is applied in the field of synthesizing amantadine, can solve the problems of long reaction time, high toxicity and influence, and achieves the effects of simple operation, pollution reduction and cost reduction.

Inactive Publication Date: 2013-01-23
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method has a high yield, the reaction time is long, and acetonitrile is a solvent, which has high toxicity, which still has a great impact on its large-scale promotion and use.

Method used

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  • Method for synthesizing amantadine

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Add 1.09g adamantane to a 250mL flask, stir evenly with 120mL dichloromethane at -30°C, add 3.8mL nitrogen dioxide, pass in ozone at a flow rate of 0.4L / min, and react for 2h. After the reaction is completed, sodium bicarbonate solution is added, the organic phase is washed to neutrality, dried with anhydrous sodium sulfate, and then rotated and evaporated to obtain 1.46 g of the product 1-Nitromantane. Take 5mmol of 1-nitromantane, 15mL of ethanol and 0.20g of catalyst FeO(OH) into a 50mL two-necked flask, heat to 78℃ under nitrogen atmosphere, slowly add 25mmol (1.2mL) 85% hydrazine hydrate, dropwise After the addition, react for 3h. After the completion of the reaction, filtration and rotary evaporation were performed to obtain 0.78 g of the product amantadine.

[0016] The product is calculated by gas spectrum detection and analysis: the conversion rate of adamantane: 99.9%; the yield of 1-nitromantane: 90.9%; the conversion rate of 1-nitromantane: 100%; the yield of ...

Embodiment 2

[0018] Change the dosage of hydrazine hydrate to 50 mmol (2.4 mL), and other operating conditions and steps are the same as in Example 1. As a result, 0.80 g of crude amantadine was obtained.

[0019] The product is calculated by gas spectrum detection and analysis: the conversion rate of 1-nitromantane: 100%; the yield of amantadine: 90.6%.

Embodiment 3

[0021] Change the dosage of hydrazine hydrate to 10 mmol (0.5 mL), and other operating conditions and steps are the same as in Example 1. As a result, 0.79 g of crude amantadine was obtained.

[0022] The product was calculated by gas spectrum detection and analysis: the conversion rate of 1-nitromantane: 100%; the yield of amantadine: 87.8%.

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Abstract

The invention discloses a method for synthesizing amantadine, which can lower the cost and reduce pollution. The method comprises the following steps: firstly, nitrifying NO2-O3, introducing ozone to react the raw material amantadine with nitrogen dioxide at low temperature, utilizing methylene dichloride as a solvent, carrying out alkaline wash after reaction, washing the organic phase until theorganic phase is neutral, drying anhydrous sodium sulfate and then carrying out rotary evaporation to obtain a product 1 nitro-amantadine; and then adding a catalyst FeO(OH) and the product 1 nitro-amantadine obtained in above step into another solvent to heat under the nitrogen atmosphere; dropwise adding hydrazine hydrate into the mixed solution; filtering the mixed liquor to remove solid afterreaction; carrying out rotary evaporation on the filter liquor to prepare the crude product of amantadine; and finally adding concentrated hydrochloric acid into the crude product of amantadine for reaction, then utilizing methylene chloride or ethyl for extraction, taking the hydrochloric acid layer, adding sodium hydroxide for basification, and carrying out filtering and drying to obtain the pure product of amantadine. The method is simple in preparation, remarkably reduces environmental pollution and has good market application prospect.

Description

Technical field [0001] The invention relates to a method for synthesizing amantadine, in particular to a method for synthesizing amantadine by reducing a nitro compound with hydrazine hydrate. Background technique [0002] Amantadine is a synthetically synthesized amino derivative of saturated tricyclodecane. It is an antiviral drug and has been proven to have obvious therapeutic effects on many diseases in the medical field. The existing industrial production method is prepared by reacting excess bromine and adamantane bromine with urea. Bromine is expensive, corrosive and difficult to recycle, causing serious pollution, and is not suitable for large-scale promotion. Nitro reduction is used to synthesize amantadine. It is reported that 1-nitromantadine is reduced by octyl viologen. After 2 hours of reaction, the yield of amantadine is 34%, the conversion rate of 24 hours is 100%, and the yield of amantadine is 100%. 98% (Park KK, et al. J. Org. Chem. 1995, 60: 6202-6204.). Alt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/38C07C209/34
Inventor 罗军马伟
Owner NANJING UNIV OF SCI & TECH