Method of preparing alpha-asarone

A kind of asarone, a certain amount of technology, applied in the field of preparation of organic compounds, can solve the problems of increasing production costs, difficult to complete dehydration reaction, unsuitable for industrial production, etc., to reduce raw material costs, reduce production costs, and shorten the synthesis route Effect

Inactive Publication Date: 2007-08-08
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Route 2 intermediates are difficult to prepare and are explosive
Routes 3 and 4 are relatively long, and the dehydration reaction is difficult to complete
In route 5, trimethoxybenzaldehyde and ethyltriphenylphosphine bromide are prepared by wittig reaction to obtain mixed olefins, and then the trans isomer product α-asarone is obtained by column chromatography, and the column chromatography method does not It is suitable for industrial production, and the cis asarone is also discarded, which affects the yield of the trans isomer product α-asarone and increases the production cost

Method used

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  • Method of preparing alpha-asarone
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  • Method of preparing alpha-asarone

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Take 15g (72mmol) of mixed alkenes to a 250ml round bottom flask, add 100ml of benzene, add the catalyst PdCl 2 (CH 3 EN) 2 372 mg (1.44 mmol), heated and refluxed and stirred for 8 hours, isomerization reached equilibrium, GC showed trans / cis=93.5 / 6.5, stopped the reaction, removed the solvent under reduced pressure, added 50 ml of anhydrous diethyl ether, stirred for 5 minutes, and filtered on silica gel powder , the solvent was removed under reduced pressure to obtain an oil, which was recrystallized from n-hexane to obtain 10.7 g of white crystals, with a yield of 71.3%, and a melting point of mp60-61°C. 1 H NMR (CDCl 3 ): δ1.88 (dd, 3H, J=1.8, 6.8Hz, -CH 3 ), 3.82 (s, 3H, -OCH 3 ), 3.86(s, 3H, -OCH 3 ), 3.88(s, 3H, -OCH 3 ), 6.09(q, 1H, J=6.8, 15.7Hz, =CH), 6.49(s, 1H, PhH), 6.65(d, 1H, -CH=, 15.7Hz), 6.94(s, 1H, PhH) .

Embodiment 2

[0036] Take 5g (24mmol) of mixed alkenes to a 100ml round bottom flask, add 25ml CH 2 Cl 2 , adding catalyst PdCl 2 (PhCN) 2 184mg (0.48mmol), stirred at room temperature for 24h, isomerization reached equilibrium, GC showed trans / cis=94.0 / 6.0, stopped the reaction, removed the solvent under reduced pressure, added 25ml of anhydrous ether, stirred for 5min, and filtered on silica gel powder , the solvent was removed under reduced pressure to obtain an oil, which was recrystallized from n-hexane to obtain 3.1 g of white crystals, with a yield of 62.0%, melting point mp60-61°C, 1 H NMR (CDCl 3 ): δ1.88 (dd, 3H, J=1.8, 6.8Hz, -CH 3 ), 3.82 (s, 3H, -OCH 3 ), 3.86(s, 3H, -OCH 3 ), 3.88(s, 3H, -OCH 3 ), 6.09(q, 1H, J=6.8, 15.7Hz, =CH), 6.49(s, 1H, PhH), 6.65(d, 1H, -CH=, 15.7Hz), 6.94(s, 1H, PhH) .

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Abstract

The invention discloses a making method of antiepileptic drug alpha-asaryl, which comprises the follwoig steps: dissolving cistron-asaryl in the solvent; adding certain quantity of palladium compound as catalyst; stirring under indoor temperature or heating condition; filtering catalyst; decompressing; condensing the reacting liquid; recrystallizing residual through ligroin or skellysolve B to obtain the product.

Description

technical field [0001] The invention relates to a method for preparing an organic compound, more specifically to a method for preparing an antiepileptic drug α-asarone. Background technique [0002] α-Asarone (trans-2,4,5-trimethoxy-1-propenylbenzene) has antitussive, expectorant, antiasthmatic, sedative, antispasmodic and anticonvulsant effects. It also has different degrees of inhibitory effect on the growth of pneumococcus, staphylococcus aureus and Escherichia coli. This product is low in toxicity and non-addictive, and the blood drug concentration reaches the peak after 15 minutes of administration, and is distributed in tissues and organs including the brain. The effect is outstanding, and it can be used as the first choice drug for preventing and treating epileptic seizures; intravenous infusion of asarone has good effects on the treatment of bronchial asthma and chronic bronchitis. In the application of Asarum injection in the treatment of bronchial asthma and chro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/215C07C41/18A61P25/08
Inventor 蒋勇军徐广宇周伊邹建卫
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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