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Preparation method for 5'-methoxylaudanosine

A technology of methoxylaudansu and phosphorus oxychloride, which is applied in the direction of organic chemistry, can solve the problems of high recovery energy consumption, high energy consumption, and expensive methyl iodide, so as to increase production rate, reduce three wastes, and reduce energy consumption. consumption effect

Inactive Publication Date: 2014-06-25
CHANGZHOU VOCATIONAL INST OF ENG
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Problems solved by technology

This method utilizes sodium methoxide solution to neutralize hydrochloride, eliminates the cumbersome unit operation, and the total yield is nearly 60%. However, condensation and cyclization in the above method produce a large amount of solvent, and recovery consumes a large amount of energy. Methyl iodide Because it is volatile and consumes a lot during the conversion, methyl iodide is expensive; a large amount of methanol is consumed to dissolve the iodide during the reduction, and the recovery energy consumption is extremely large

Method used

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  • Preparation method for 5'-methoxylaudanosine
  • Preparation method for 5'-methoxylaudanosine

Examples

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Embodiment 1

[0021] Preparation of 3,4-dihydro-6,7-2methoxy-1-[2-(3,4,5-trimethoxyphenyl)ethyl]isoquinoline hydrochloride

[0022] Add 600mL xylene, 22.6g (0.1mol) of 3,4,5-trimethoxyphenylacetic acid and 18.1g (0.1mol) of 3,4-dimethoxyphenethylamine successively in a 1L four-necked flask, and reflux Divide water for 5 hours, cool to 80-85°C, add 16.9g (0.11mol) of phosphorus oxychloride dropwise, keep warm for about 3-4 hours after dropping, after wave layer chromatography detection shows that the raw materials disappear, cool to 0-5°C, Filter, wash the filter cake with 50 mL of ethyl acetate, and dry to obtain off-white solid V (39.0 g, 96.2%), mp 109.7~111.3 °C 1,2,3,4-tetrahydro-6,7-dimethoxy - Preparation of 1-[2-(3,4,5-trimethoxyphenyl)ethyl]isoquinoline

[0023] Add 600mL of methanol and 2.3g (0.1mol) of sodium metal to a 1L four-neck flask in turn, stir until the sodium disappears, then cool to room temperature, add 40.6g (0.1mol) of compound V, stir for 10min to obtain a white tu...

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Abstract

The invention relates to the field of medicine synthesis, and specifically relates to a preparation method for a nondepolarizer mivacurium chloride intermediate 5'-methoxylaudanosine. The preparation method is characterized by taking 3,4,5-trimethoxyphenylacetic acid and 3,4-dimethoxyphenethylamine as raw materials, employing a condensation cyclization one-pot process to prepare 3,4-dihydro-6,7-dimethoxy-1-[2-(3,4,5-trimethoxyphenyl)ethyl]isoquinoline hydrochloride, and then performing potassium borohydride reduction and dimethyl sulphate methylation. The preparation method has the advantages of being mild in reaction conditions, good in product quality, high in yield, low in production cost and the like.

Description

1. Technical field [0001] The present invention relates to a kind of preparation method of 5'-methoxylaudansu, relate in particular to the method for using 3,4,5-trimethoxyphenylacetic acid as raw material to synthesize 5'-methoxylaudansu. 2. Background technology [0002] The English name of 5'-methoxylaudanosine is 5'-methoxylaudanosine, and its molecular formula is C 22 h 29 NO 5 , is the key intermediate for the synthesis of short-acting benzylisoquinoline non-depolarizing muscle relaxant Mivacurium Chloride. [0003] At present, the methods for synthesizing 5'-methoxylaudansin mainly include: [0004] John B Stenlake et al. used 3,4,5-trimethoxyphenylacetic acid and 3,4-dimethoxyphenethylamine to condense under solvent-free conditions at about 200 ° C, and the obtained condensate was added to toluene with trichloroxy Phosphorous cyclization to obtain 3,4-dihydro-6,7-dimethoxy-1-[2-(3,4,5-trimethoxyphenyl) ethyl] isoquinoline hydrochloride, and then Reduction of the...

Claims

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Application Information

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IPC IPC(8): C07D217/20
CPCC07D217/20
Inventor 贺新薛叙明李树白刘长春周敏茹
Owner CHANGZHOU VOCATIONAL INST OF ENG
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