CS227998B1 - Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine - Google Patents
Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine Download PDFInfo
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- CS227998B1 CS227998B1 CS749582A CS749582A CS227998B1 CS 227998 B1 CS227998 B1 CS 227998B1 CS 749582 A CS749582 A CS 749582A CS 749582 A CS749582 A CS 749582A CS 227998 B1 CS227998 B1 CS 227998B1
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- hydrochloride
- dihydroxyphenyl
- ethylamine
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- homoveratrylamine
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Description
(54) Způsob přípravy hydrochloridu 2-(3,4-dihydroxyfenyl)-etylaminu(54) A process for the preparation of 2- (3,4-dihydroxyphenyl) -ethylamine hydrochloride
Hydrochlorid 2-(3,4-dihydroxyfenyl)-etylaminu se používá ve farmacii jako protišokový preparát v injekční formě.2- (3,4-Dihydroxyphenyl) -ethylamine hydrochloride is used in pharmacy as an anti-shock preparation in injectable form.
Syntetických postupů k přípravě této látky je řada, ale dva jsou ekonomicky i technologicky nejschůdnějSí. První je postup podle amerického patentového spisu č. 2 749 275 z r. 1956 a druhý Ss. AO č. 224 123 ěs. autora. Oba dva postupy vycházejí z homoveratrylaminu, který se ětěpí azeotropickou kyselinou bromovodíkovou na 2-(3,4-dihydroxyfenyl)-etylamin hydrobromid. Oba postupy se pak liší způsobem izolace 2-(3,4-dihydroxyfenyl)-etylamin hydrochloridu.There are many synthetic processes for the preparation of this substance, but two are the most economically and technologically feasible. The first is the process described in U.S. Patent 2,749,275 of 1956 and the second is U.S. Pat. AO No 224 123 es. author. Both processes start from homoveratrylamine, which is cleaved by azeotropic hydrobromic acid to give 2- (3,4-dihydroxyphenyl) -ethylamine hydrobromide. The two procedures then differ in the manner of isolating 2- (3,4-dihydroxyphenyl) -ethylamine hydrochloride.
Nevýhoda obou postupů, tj. podle amerického patentového spisu S. 2 749 275 a čs. AO Č. 224 123 spočívá v tom, že jsou vícestupňové, tedy výtěžkově i pracností náročné.A disadvantage of both processes, i.e. according to U.S. Pat. No. 2,749,275 and U.S. Pat. AO No. 224 123 lies in the fact that they are multistage, ie in terms of yield and labor intensive.
Postup podle amerického patentového spisu č. 2 749 275 spočívá v těchto syntetických stupních: homoveratrylamin je surovinou, homoveratrylamin hydrochlorid, 2-(3,4-dihydroxyfenyl)-etylamin hydrobromid, trojnásobná krystalizace této látky z koncentrované kyseliny chlorovodíkové za vzniku 2-(3,4-dihydroxyfenyl)-etylamin hydrochloridu. Tento postup je pětistupňový.The process of U.S. Pat. No. 2,749,275 consists of the following synthetic steps: homoveratrylamine is a raw material, homoveratrylamine hydrochloride, 2- (3,4-dihydroxyphenyl) ethylamine hydrobromide, triple crystallization of this material from concentrated hydrochloric acid to give 2- (3). 4-dihydroxyphenyl) -ethylamine hydrochloride. This is a five-step procedure.
Podle čs. AO č. 224 123 obsahuje postup následující stupně: homoveratrylamin je surovinou, homoveratrylamin hydrochlorid, 2-(3,4-dihydroxyfenyl)-etylamin hydrobromid, převede ní na bázi a vyloučení surového hydrochloridu, krystalizace surové látky. Tento postup je čtyřstupňový.According to MS. AO No. 224 123 discloses the process of the following steps: homoveratrylamine is a raw material, homoveratrylamine hydrochloride, 2- (3,4-dihydroxyphenyl) -ethylamine hydrobromide, conversion based on and precipitation of the crude hydrochloride, crystallization of the crude material. This is a four-step procedure.
Nevýhody těchto vícestupňových syntéz odstraňuje postup podle vynálezu, který spočívá v tom, že se homoveratrylamin hydrochlorid podrobí 150- až 200hodinovému štěpení azeotropickou kyselinou chlorovodíkovou při teplotě 80 až ,10 °C. Po této době se roztok ochladí a surový 2-(3,4-dihydroxyfenyl)-etylamin hydrochlorid se vyloučí v krystalické formě. Překrystalizováním této látky se získá žádaná substance použitelné pro farmaceutické účely. Surová látka tímto postupem připravená vzniká ve výtěžku 90 až 95 % teorie.The disadvantages of these multi-step syntheses are eliminated by the process according to the invention, which comprises subjecting homoveratrylamine hydrochloride for 150 to 200 hours with azeotropic hydrochloric acid at a temperature of 80-10 ° C. After this time, the solution was cooled and the crude 2- (3,4-dihydroxyphenyl) -ethylamine hydrochloride precipitated in crystalline form. Recrystallization of this material yields the desired substance useful for pharmaceutical purposes. The crude product is obtained in a yield of 90 to 95% of theory.
Následující příklad provedení uvedený způsob podle vynálezu pouze dokládá, ale nijak neomezuje.The following exemplary embodiment illustrates the method of the invention, but is not limited thereto.
Příklad provedeníExemplary embodiment
100 g homoveratrylaminu hydrochloridu se zahřívá za občasného zamíchání při teplotě 95 až 100 °C v roztoku 750 ml koncentrované kyselině chlorovodíkové a 250 ml vody po dobu 150 hodin. Po této době se reakční roztok ochladí a vyloučené krystaly surového 2-(3,4-dihydroxyfenyl)-etylamin hydrochloridu se odsají a na filtru promyjí acetonem. Výtěžek surové látky je 80 g, tj. 91,8 teorie. Po krystalizaci ve zředěné kyselině chlorovodíkové se získá vyhovující substance pro farmaceutické použití.100 g of homoveratrylamine hydrochloride are heated with occasional stirring at a temperature of 95 to 100 ° C in a solution of 750 ml of concentrated hydrochloric acid and 250 ml of water for 150 hours. After this time, the reaction solution was cooled and the precipitated crude 2- (3,4-dihydroxyphenyl) -ethylamine hydrochloride crystals were filtered off with suction and washed with acetone on the filter. Yield of crude material is 80 g, i.e. 91.8 theory. After crystallization in dilute hydrochloric acid, a suitable substance for pharmaceutical use is obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS749582A CS227998B1 (en) | 1982-10-22 | 1982-10-22 | Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS749582A CS227998B1 (en) | 1982-10-22 | 1982-10-22 | Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine |
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| Publication Number | Publication Date |
|---|---|
| CS227998B1 true CS227998B1 (en) | 1984-05-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS749582A CS227998B1 (en) | 1982-10-22 | 1982-10-22 | Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025082547A1 (en) * | 2024-06-11 | 2025-04-24 | 中国科学院广州能源研究所 | Method for synthesizing dopamine hydrochloride from eugenol |
-
1982
- 1982-10-22 CS CS749582A patent/CS227998B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025082547A1 (en) * | 2024-06-11 | 2025-04-24 | 中国科学院广州能源研究所 | Method for synthesizing dopamine hydrochloride from eugenol |
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