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Method for preparing ambroxol hydrochloride

A technology of ambroxol hydrochloride and o-aminodibromobenzaldehyde, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of imino compounds, etc., can solve problems such as safety and environmental protection or cost without much industrial value, and achieve The safety level is lowered, the operation is simple, and the yield is improved.

Inactive Publication Date: 2019-07-05
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

This new method involves reacting aniline-2-bonded bone marrow extracts from animal tissues called oleonardium together with other chemical substances like ammoniacal nitrite solution. These reactions are done at room temperature without any added metals such as zinc hydride or tin chloroformate. By repeating experimentations it was discovered how much more material could be obtained when using this novel technique compared to previous methods. Additionally, there were no concerns about producing unsafe products during the procedure due to the presence of excessive amounts of iron powder commonly included in existing processes. Overall, this technology provides safer and better ways to make medicines while minimizing environmental impact.

Problems solved by technology

Technological Problem addressed in this patented technical problem relates to improves on existing ways of producing ambrisols called ambronics® from 2-(methylenebrolimidoazole). These new techniques involve chemistry involving specific reactions between certain substances like 3'-(2',3-dimensionally linked nucleotides), specifically guided by enzymes involved in metabolism. However, current methodologies require expensive equipment and hazardous materials while still being effective at removing impurities generated due to biodegradations caused by natural sources.

Method used

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  • Method for preparing ambroxol hydrochloride
  • Method for preparing ambroxol hydrochloride
  • Method for preparing ambroxol hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of ambroxol hydrochloride

[0045] Add 50g (0.18mol) of o-aminodibromobenzaldehyde, 20.7g (0.18mol) of (E)-p-aminocyclohexanol, 200ml of toluene, 0.5g (0.0041mol) of DMAP into a 500ml reaction flask, and heat up to 100°C for reaction After 5 hours, TLC followed the progress of the reaction. After the reaction was completed, it was cooled to 20° C. and crystallized for 2 hours. After cooling and suction filtration, the filter cake was rinsed with a small amount of solvent to obtain 66 g of white powdery ambroxol base, with a yield of 98.5%.

[0046] In the reaction bottle of 500ml, add the ambroxol base (0.175mol) of 66g, methyl alcohol 300ml, add formic acid 30ml (0.652mol) after replacing nitrogen, 5% palladium carbon 0.5g (0.00024mol), be warming up to 40 ℃, react After 5 hours, the reaction was replaced with nitrogen. After the reaction solution was concentrated to 130ml, it was cooled and crystallized at 10°C for 2h, and filtered to ...

Embodiment 2

[0048] Embodiment 2: the preparation of Ambroxol Hydrochloride

[0049] Add 50g (0.18mol) of o-aminodibromobenzaldehyde, 20.7g (0.18mol) of (E)-p-aminocyclohexanol, 200ml of toluene, 0.75g (0.0065mol) of DMAP into a 500ml reaction flask, and heat up to 100°C for reaction After 5 hours, TLC followed the progress of the reaction. After the reaction was completed, it was cooled to 20° C. and crystallized for 2 hours. After cooling and suction filtration, the filter cake was rinsed with a small amount of solvent to obtain 66 g of white powdery ambroxol base, with a yield of 98.5%.

[0050] In the reaction flask of 500ml, add the ambroxol base (0.175mol) of 66g, methyl alcohol 300ml, add formic acid 30ml (0.652mol) after replacing nitrogen, 5% palladium carbon 2.1g (0.001mol), be warming up to 40 ℃, react After 5 hours of reaction, nitrogen replacement was carried out. After the reaction solution was concentrated to 130ml, it was cooled and crystallized at 10°C for 2h, and 64g o...

Embodiment 3

[0052] Embodiment 3: the preparation of ambroxol hydrochloride

[0053] Add 50g (0.18mol) of o-aminodibromobenzaldehyde, 20.7g (0.18mol) of (E)-p-aminocyclohexanol, 200ml of toluene, 1.0g (0.0082mol) of DMAP into a 500ml reaction flask, and heat up to 100°C for reaction After 5 hours, TLC followed the progress of the reaction. After the reaction was completed, it was cooled to 20° C. and crystallized for 2 hours. After cooling and suction filtration, the filter cake was rinsed with a small amount of solvent to obtain 66 g of white powdery ambroxol base, with a yield of 98.5%.

[0054] In a 500ml reaction flask, add 66g of ambroxol base (0.175mol), methanol 300ml, add formic acid 30ml (0.652mol) after nitrogen replacement, palladium chloride 0.1g (0.00056mol), heat up to 40°C, and react 5 Nitrogen replacement after 1 hour reaction. After the reaction solution was concentrated to 130ml, it was cooled and crystallized at 10°C for 2h, and 63.7g of ambroxol was obtained by filtrat...

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Abstract

The invention discloses a method for preparing ambroxol hydrochloride. The method comprises the steps of (1) using o-aminodibromobenzaldehyde and trans-p-aminocyclohexanol as raw materials, using 4-dimethylaminopyridine as a catalyst, carrying out a condensation reaction in a reaction solvent, and after the reaction, obtaining a compound (I) by post-treatment; (2), using formic acid or formate which is cheap and easily availableas a reducing agent, using palladium carbon, palladium chloride, raney nickel or platinum carbonas a catalyst, making the compound (I) be subjected to a reduction reaction in a reaction solvent, and after the completion of the reaction, obtaining a compound (II) by post-treatment; (3), making the compound (II) be reacted with hydrochloric acid in a reaction solvent,and after the completion of the reaction,obtaining a compound (III) by post-treatment.The method adopts o-aminodibromobenzaldehyde and trans-p-aminocyclohexanol as raw materials, uses condensation and reduction of the formic acid or formate, and forms salt from hydrochloric acid to obtain the ambroxol hydrochloride. Themethod is safe and environmentally friendly, has small pollution, good economic benefit and simple operation and is suitable for industrial production.

Description

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Claims

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Application Information

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Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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