CS227998B1 - Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine - Google Patents

Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine Download PDF

Info

Publication number
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
Authority
CS
Czechoslovakia
Prior art keywords
hydrochloride
dihydroxyphenyl
ethylamine
preparation
homoveratrylamine
Prior art date
Application number
CS749582A
Other languages
Czech (cs)
Inventor
Josef Rndr Budnik
Original Assignee
Budnik Josef
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Budnik Josef filed Critical Budnik Josef
Priority to CS749582A priority Critical patent/CS227998B1/en
Publication of CS227998B1 publication Critical patent/CS227998B1/en

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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)

PŘEDMĚT VYNÍLEZUOBJECT OF THE INVENTION Způsob přípravy 2-(3,4-dihydroxyfenyl)-etylamin hydrochloridu vyznačený tím, že se homoveratrylamin hydrochlorid ponechá reagovat s azeotropickou kyselinou chlorovodíkovou po dobu 150 až 200 hodin při teplotě 80 až 110 °C.Process for preparing 2- (3,4-dihydroxyphenyl) -ethylamine hydrochloride, characterized in that homoveratrylamine hydrochloride is reacted with azeotropic hydrochloric acid for 150 to 200 hours at a temperature of 80 to 110 ° C.
CS749582A 1982-10-22 1982-10-22 Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine CS227998B1 (en)

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

Publications (1)

Publication Number Publication Date
CS227998B1 true CS227998B1 (en) 1984-05-14

Family

ID=5424199

Family Applications (1)

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

Country Status (1)

Country Link
CS (1) CS227998B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
KR890000763B1 (en) Method for preparing 4'-demethyl-epipodophyllotoxin-β-D-ethylidene-glucoside and its acyl derivative
EP1334963B1 (en) Process for producing nateglinide crystal
JPH05148206A (en) Preparation of monoester-monoamide, monoacid- monoamide and bisamide of once and twice substituted malonic acid, compound prepared by the process
HU206671B (en) Process for purifying melphalane
US4246428A (en) Method for separation of diastereoisomeric 3-(3,4-dibenzyloxyphenyl)serine
US3116332A (en) Resolution of racemic aminoisopropanol
CS227998B1 (en) Preparation of hydrochloride of 2-/3,4-dihydroxyphenyl/ethylamine
JP2503056B2 (en) Method for producing 1,6-di (Nup3) -cyano-Nup1) -guanidino) hexane
US2370015A (en) Derivatives of tertiary amino aliphatic acids
HU178248B (en) Process for producing 1-2-amino-butanol salts of phenyl-glycine derivatives,and in a given case for deliberating the amino acid from the salt
US2921959A (en) Process of resolving dl-serine
US5260462A (en) Purification of tauroursodesoxycholic acid dihydrate
US2441141A (en) Optically active basic amino acid salts of a stereoisomer of cis-2-(4'-carboxy-butyl)-3:4-ureido-tetrahydrothiophene
US1633392A (en) Sedative and hypnotic ureides
KR910003614B1 (en) Process for preparing cis-3,3,5-trimethyl-cyclohexyl-d,l-alpha-(3-pyridinecarboxy)-phenylacetate
US3090785A (en) New process for preparing acylated
DE1645918B2 (en) PROCESS FOR THE PREPARATION OF THE SALICYL ACID ESTER OF BETA-PYRIDYLCARBINOL
RU2051905C1 (en) Process for preparing dimethylamino-1,3-bis (phenylsulfonylthio) propane
US5326908A (en) Process for the preparation of asparagine
SU374936A1 (en) Method of preparing mono-n-substituted piperazine
CA1322626C (en) Process for the preparation of aspartylphenylalanine methyl ester from n-formylaspartylphenylalanine methyl ester
JP2856331B2 (en) Method for producing 2,2-diamino-1,1-binaphthyl
SU57506A1 (en) The method of obtaining 1-phenyl-3-methyl-pyrazolone
US2517585A (en) N-(2-cyanoethyl)-2-pyrrolidone-5-carboxylic acid and methods for its preparation
SU432150A1 (en) METHOD OF OBTAINING WATER SOLUBLE 9-SUBSTITUTED 6-MERCAPTOPURINS