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Preparation method of adrenalone hydrochloride

A technology of epinephrine hydrochloride and epinephrine, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc.

Active Publication Date: 2017-05-31
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are few reports on the synthesis process of epinephrine hydrochloride in domestic literature

Method used

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  • Preparation method of adrenalone hydrochloride
  • Preparation method of adrenalone hydrochloride
  • Preparation method of adrenalone hydrochloride

Examples

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Embodiment 1

[0032] The present embodiment relates to a kind of preparation method of epinephrine hydrochloride, comprises the steps:

[0033] 1) Add 10g (0.054mol) of chloroacetylcatechol, 39g of ethanol solution of methylamine (containing 30% methylamine, 0.378mol) and 0.3g (0.0008mol) of tetrabutylammonium iodide into a 250ml three-necked reaction flask Stir at 30°C to make the material uniform. Nitrogen was introduced to replace the air in the reaction flask 4 times, and nitrogen was passed through the whole process, and reacted at a temperature of 30° C. for 6 hours until the reaction solution was gray-green. Stop the reaction, filter to obtain a gray-green solid, wash the gray-green solid with absolute ethanol and drain it to obtain a gray-green solid tidal product of epinephrine;

[0034] 2) Add the gray-green solid tidal product of epinephrine into a mixed solution of ethanol and concentrated hydrochloric acid (30ml of ethanol, 9ml of concentrated hydrochloric acid) for salt forma...

Embodiment 2

[0037] The present embodiment relates to a kind of preparation method of epinephrine hydrochloride, comprises the steps:

[0038] 1) Add 10g (0.054mol) of chloroacetylcatechol, 61.3g of ethanol solution of methylamine (containing 30% methylamine, 0.594mol) and 0.3g (0.0008mol) of tetrabutylammonium iodide to 250ml three-port reaction In the bottle, stir at 30°C to make the material uniform. Nitrogen was introduced to replace the air in the reaction bottle for 4 times, and then the reaction flask was protected by nitrogen, and reacted at a temperature of 30° C. for 4 hours. until the reaction solution is gray-green. Stop the reaction, filter to obtain a gray-green solid, wash the gray-green solid with absolute ethanol and drain it to obtain epinephrine;

[0039] 2) Add the gray-green solid tidal product of epinephrine into a mixed solution of ethanol and concentrated hydrochloric acid (30ml ethanol, 9ml concentrated hydrochloric acid) for salt formation reaction, stir, and ad...

Embodiment 3

[0042] The present embodiment relates to a kind of preparation method of epinephrine hydrochloride, comprises the steps:

[0043] 1) Add 10g (0.054mol) of chloroacetylcatechol, 39g of ethanol solution of methylamine (containing 30% methylamine, 0.378mol) and 0.6g (0.0012mol) of tetrabutylammonium iodide into a 250ml three-necked reaction flask Stir at 40°C to make the material uniform. The air in the reaction flask was replaced by nitrogen gas for 4 times, and then protected by nitrogen gas, and the reaction was carried out at 30° C. for 5 h. until the reaction solution is gray-green. Stop the reaction, filter to obtain a gray-green solid, wash the gray-green solid with absolute ethanol and drain it to obtain epinephrine;

[0044] 2) Add the gray-green solid tidal product of epinephrine into a mixed solution of ethanol and concentrated hydrochloric acid (30ml ethanol, 9ml concentrated hydrochloric acid) for salt formation reaction, stir, and adjust the pH of the reaction sol...

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Abstract

The invention relates to a preparation method of adrenalone hydrochloride. In a process of preparing the adrenalone hydrochloride from chloracetyl catechol and methylamine, reaction is controlled to be carried out in an alcohol solution and tetrabutylammonium bromide or tetrabutylammonium iodide is selected as a phase transfer catalyst. According to the method provided by the invention, the reaction is controlled to be carried out in the alcohol solution and sufficient proceeding of the reaction is promoted; meanwhile, the tetrabutylammonium bromide or the tetrabutylammonium iodide is added to be used as the phase transfer catalyst, so that the reaction is accelerated, the reaction time is shortened and the accumulation of impurities is reduced. The adrenalone hydrochloride with high quality can be prepared at a single time without the need of refining, and a high-quality intermediate is provided for preparation of L-adrenaline.

Description

technical field [0001] The invention relates to the technical field of organic synthesis of medicines, in particular to a preparation method of epinephrine hydrochloride. Background technique [0002] The chemical name of epinephrine hydrochloride is: 1-(3,4-dihydroxyphenyl)-2-methylaminoethanone hydrochloride, which is an intermediate for the preparation of epinephrine. There are few domestic literature reports on the synthesis process of epinephrine hydrochloride. Since epinephrine hydrochloride is an intermediate in the synthesis of epinephrine drugs, it is necessary to study and optimize its synthesis process to facilitate industrial production. The molecular structure of epinephrine is as follows: [0003] [0004] WO 2009 / 004593 reports the synthesis process of epinephrine, the intermediate of which is not epinephrine but benzyladrenaline, and then adrenaline is prepared by hydrogenation catalytic reaction. The structural formula of benzyladrenone is as follows: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/16
CPCC07C221/00C07C225/16
Inventor 韦亚锋郑爱张瑾李立标林文龙
Owner BENGBU BBCA MEDICINE SCI DEV
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