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Preparation method of quaternary ammonium salts of methyl ammonium bromide

A technology of methyl ammonium bromide and quaternary ammonium salt, which is applied in chemical instruments and methods, preparation of amino compounds from amines, organic chemistry, etc., can solve the problems of low exchange efficiency, narrow application range and high preparation cost, and achieves improved safety. sexual effect

Active Publication Date: 2012-02-08
CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the bromination reagent used in this method is only suitable for sulfonic acid radical quaternary ammonium salts, the application range is narrow, and the exchange efficiency is low, resulting in higher preparation costs of the product

Method used

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  • Preparation method of quaternary ammonium salts of methyl ammonium bromide
  • Preparation method of quaternary ammonium salts of methyl ammonium bromide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1, the preparation of methyl diethyl hexadecyl ammonium bromide

[0042] A. Treatment of Brominated Strongly Basic Anion Exchange Resin

[0043] Add 400ml of resin to a glass chromatography column, add 1L of absolute ethanol to soak for 2h, wash the resin with deionized water until there is no alcohol smell, then soak in 1L of 2M hydrochloric acid for 2h, wash with deionized water until neutral, and wash with 2M hydrogen Wash with sodium oxide aqueous solution until there are no chloride ions (detection method: 2-3 drops of effluent, adjust the acidity with dilute nitric acid, add silver nitrate dropwise without precipitation), add deionized water to wash until neutral, and then wash the resin with saturated sodium bromide aqueous solution To pH = 7, add deionized water to wash until there is no bromide ion (detection method: take 2-3 drops of the effluent, add 1-2 drops of silver nitrate solution, no precipitation is formed);

[0044] B, the preparation of ...

Embodiment 2

[0047] Embodiment 2, the preparation of trimethyl (2-pentadecyl) eicosyl ammonium bromide

[0048] A. Treatment of Brominated Strongly Basic Anion Exchange Resin

[0049] Add about 220ml of resin used in Example 1 into a glass chromatography column, add 2L of absolute ethanol and soak for 5h, wash the resin with deionized water until there is no alcohol smell, and wash with 2M aqueous sodium hydroxide solution until there is no halogen ion (detection method: 2-3 drops of the effluent, adjust the acidity with dilute nitric acid, add dropwise silver nitrate (no precipitation), wash with deionized water until neutral, then wash the resin with saturated sodium bromide aqueous solution to pH = 7, wash with deionized water until no bromine Ion (detection method: take 2-3 drops of effluent, add 1-2 drops of silver nitrate solution, no precipitation is formed);

[0050] B, the preparation of trimethyl (2-pentadecyl) eicosyl ammonium bromide

[0051] At room temperature, 3.6g (5.2mmol)...

Embodiment 3、4

[0053] Example 3, 4,4'-[3α, 17β-bis(acetoxy)-5α-androstane-2β, 16β-dimethyl]-bis(1,1-dimethyl-piperazinium) Preparation of dibromide

[0054] A. Treatment of Brominated Strongly Basic Anion Exchange Resin

[0055] Processing method is with embodiment 1;

[0056] B, 4,4'-[3α,17β-bis(acetoxy)-5α-androstane-2β,16β-dimethyl]-bis(1,1-dimethyl-piperazinium)dibromide Compound preparation

[0057] At room temperature, 5.0 g (5.2 mmol) of 4,4'-[3α,17β-bis(acetyloxy)-5α-androstane-2β,16β-dimethyl]-bis(1,1-dimethyl Base-piperazinium) di-(p-toluenesulfonate) was dissolved in 300ml deionized water, took 220ml treated bromine-type strong basic anion exchange resin and packed it into a column, passed the above aqueous solution through the column, and washed with 300ml deionized water After removal, the effluent was collected and concentrated to dryness under reduced pressure at 60°C-80°C to obtain 3.7 g of white solid, melting point: 273°C-274°C (decomposition), yield 92.5% (HPLC>99.9%)....

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Abstract

The invention provides a method for preparing quaternary ammonium salts of methyl ammonium bromide without using methyl bromide. The quaternary ammonium salts of methyl ammonium bromide are prepared by dissolving quaternary ammonium compounds in bromine highly basic anion exchange resin, and carrying out ion exchange. According to the invention, the usage of methyl bromide in preparing quaternary ammonium salts of methyl ammonium bromide is effectively avoided, the safety of preparing quaternary ammonium salts of methyl ammonium bromide is signally improved, the characteristics of nontoxicity and innocuousness, and environmental protection are achieved, the product yield is high, the purity of the product reaches to more than 99.8 %, and the requirements of various pharmacopeias for medicine quality are satisfied effectively.

Description

technical field [0001] The invention relates to the fields of pharmaceutical chemistry and organic chemistry preparation, in particular to a method for preparing methyl ammonium bromide quaternary ammonium salts by means of ion exchange. Background of the invention [0002] Methylammonium bromide quaternary ammonium salt compounds are widely used in the field of medicine, and its representative compounds mainly include pipecuronium bromide, vecuronium bromide, glycopyrronium bromide, etc. [0003] Hungarian patent 165,000 discloses the synthesis method of pipecuronium bromide, the structure of which is shown in formula VII. The method takes 2α, 3α, 16α, 17α-diepoxy-17-acetoxy-5α-androstane as the starting material to obtain the final product through multi-step synthesis. The final step is to react the product of the penultimate step with methyl bromide in acetone or ether to form a quaternary ammonium salt. [0004] Formula VII [0005] The synthesis method of vecuroniu...

Claims

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Application Information

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IPC IPC(8): C07J43/00C07D211/42C07C211/63C07C209/68B01J41/10
Inventor 王颖袁明旭孙红岩
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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