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New method for synthesizing codeine from morphine

A new method and technology for morphine, applied in the field of morphine synthesis of codeine, can solve the problems of high price of phenyltrimethylammonium chloride, difficult preparation, inconvenient storage and transportation, etc.

Inactive Publication Date: 2005-03-30
SICHUAN INDAL INST OF ANTIBIOTICS CHINA NAT PHARMA GROUP CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The only disadvantage is that the price of phenyltrimethylammonium chloride is high and it is not easy to prepare
The preparation process needs to use methyl chloride, and methyl chloride is a gas under normal pressure, so it is inconvenient to store and transport

Method used

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  • New method for synthesizing codeine from morphine
  • New method for synthesizing codeine from morphine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The preparation of embodiment 1 phenyl trimethyl ammonium methyl sulfate

[0017] Put 121.0 g (1.00 Mol) of N,N-dimethylaniline and 300 ml of toluene into the reaction vessel, stir and heat to 40°C, start adding 126.0 g (1.00 Mol) of dimethyl sulfate dropwise, and control the temperature at 30-50 ℃, dripped in about 30 minutes, then continued to stir for 2 hours, cooled to 5 ℃ for 4 hours to crystallize under stirring, filtered, washed with toluene, and dried to obtain 225.0 g of product, mp 123-125 ℃, yield 91.1%.

Embodiment 2

[0018] The preparation of embodiment 2 codeine

[0019] Put 75.1g (0.200Mol) of morphine hydrochloride, 59.3g (0.240Mol) of phenyltrimethylammonium methylsulfate, 138.0g (1.00Mol) of potassium carbonate, and 820ml of toluene into the reaction vessel, heat and reflux for 2 to 8 hours while stirring , filter, evaporate toluene under reduced pressure, add water to the solid and acidify to PH5~6, remove N,N-dimethylaniline by steam distillation, decolorize activated carbon, concentrate the product solution under reduced pressure, adjust pH to 9~12 with sodium hydroxide solution , crystallized, filtered, washed and dried to obtain 56.3 g of the product, the HPLC chromatographic purity was greater than 99.5%, and the yield was 94.1%.

Embodiment 3

[0020] The preparation of embodiment 3 codeine

[0021] Put 71.2g of morphine base (content 84.1%, 0.200Mol), 59.3g (0.240Mol) of phenyltrimethylammonium methyl sulfate, 110.4g (0.800Mol) of potassium carbonate, and 820ml of toluene into the reaction vessel, and heat to reflux under stirring 2 to 8 hours, filter, evaporate toluene under reduced pressure, add water and acidify the solid to pH 5~6, remove N,N-dimethylaniline by steam distillation, decolorize with activated carbon, concentrate the product solution under reduced pressure, sodium hydroxide solution Adjust the pH to 9-12, crystallize, filter, wash, and dry to obtain 56.6 g of the product. The HPLC chromatographic purity is greater than 99.5%, and the yield is 94.6%.

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Abstract

The invention provides a method for composing codeine by morphine. By the inventino, morphine, phenylthrimethyl methylamine sulfate and alkali metal carbonas are dissolved in a hydrocarbon dissolvant to proceed reactino 2-8 hours in temp. 80-120 deg.C, then to be separated to obtain codeine.

Description

technical field [0001] The present invention relates to a novel process for the synthesis of codeine from morphine. Background technique [0002] Codeine is a pain reliever and cough suppressant. It is a methyl derivative of morphine. The content in natural opium is about 1%. Because of its low content in nature, most of the codeine currently used in the world is derived from semi-synthetic methods. First, morphine is extracted from opium or CPS (poppy straw concentrate), and then the phenolic hydroxyformazine on the morphine molecule is extracted. Kylation to get codeine. [0003] The currently known method for semi-synthesizing codeine is to react morphine with a methylating agent and then separate to obtain codeine. The methylating agents used include dimethyl sulfate, methyl chloride, phenyltrimethylammonium hydroxide, phenyltrimethylammonium ethoxylate, phenyltrimethylammonium bromide, phenyltrimethylammonium chloride, etc. . Among the above numerous methods, rela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D489/02
Inventor 艾林陈晓源张乐
Owner SICHUAN INDAL INST OF ANTIBIOTICS CHINA NAT PHARMA GROUP CORP