DE619756C - Process for the preparation of diamino alcohols of the aromatic series - Google Patents

Process for the preparation of diamino alcohols of the aromatic series

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Publication number
DE619756C
DE619756C DEC48932D DEC0048932D DE619756C DE 619756 C DE619756 C DE 619756C DE C48932 D DEC48932 D DE C48932D DE C0048932 D DEC0048932 D DE C0048932D DE 619756 C DE619756 C DE 619756C
Authority
DE
Germany
Prior art keywords
preparation
aromatic series
alcohols
diamino alcohols
diamino
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEC48932D
Other languages
German (de)
Inventor
Dr Heinrich Hornstein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CHEMISCHE FABRIKEN DR JOACHIM
Original Assignee
CHEMISCHE FABRIKEN DR JOACHIM
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 CHEMISCHE FABRIKEN DR JOACHIM filed Critical CHEMISCHE FABRIKEN DR JOACHIM
Priority to DEC48932D priority Critical patent/DE619756C/en
Application granted granted Critical
Publication of DE619756C publication Critical patent/DE619756C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Diaminoalkoholen der aromatischen Reihe Gegenstand des Hauptpatents 6115oi ist ein Verfahren zur Herstellung von Abkömmlingen des optisch aktiven oder racemischen i-Phenyl-2-methylaminopropan-i-ols durch Umsetzung dieser Verbindungen mit Halogeniden oder Sulfonsäureestern von Dialkylaminoäthanolen oder den Salzen dieser Verbindungen.Process for the preparation of diamino alcohols of the aromatic series The subject of the main patent 6115oi is a process for the production of descendants of the optically active or racemic i-phenyl-2-methylaminopropan-i-ol by reaction of these compounds with halides or sulfonic acid esters of dialkylaminoethanols or the salts of these compounds.

Es wurde gefunden, daß man nach einem analogen Verfahren auch die Diaminoalkohole der aromatischen Reihe der allgemeinen Zusammensetzung worin R einen Dialkylarninoalkylrest mit Ausnahme von Dialkylaminoäthyl darstellt, herstellen kann. Zu diesem Zweck wird i-Phenyl-2-methylaminopropan-i-ol mit Sulfonsäureestern oder Halogeniden von Dialkylaminoalkoholen mit Ausnahme von Dialkylaminoäthanol oder deren Salzen, gegebenenfalls bei Anwesenheit von säurebindenden Mitteln, zur Umsetzung gebracht.It has been found that the diamino alcohols of the aromatic series of the general composition can also be obtained by an analogous process wherein R is a dialkylaminoalkyl radical with the exception of dialkylaminoethyl, can produce. For this purpose, i-phenyl-2-methylaminopropan-i-ol is reacted with sulfonic acid esters or halides of dialkylamino alcohols with the exception of dialkylaminoethanol or their salts, optionally in the presence of acid-binding agents.

Die neuen Verbindungen sollen für therapeutische Zwecke oder als Zwischenprodukte zur Herstellung neuer Heilmittel dienen. Beispiel i i-Phenyl-2-(methyl- [diäthylamin@propyl] )-aminopropan-i-ol 33o Teile Ephedrin werden in i 5 5 Teilen Benzol gelöst und mit i5o Teilen i-Diäthylamino-3-chlorpropan (C2 H5) 2 # N # CH. # CH2 # CH2 # Cl versetzt. Die Lösung wird io Stunden rückfließend erhitzt, wobei sich ein Kristallbrei von salzsaurem Ephedrin abscheidet. Von diesem wird abgetrennt und das Filtrat zur Vervollständigung der Umsetzung noch 3 Stunden im geschlossenen Gefäß im siedenden Wasserbad erhitzt. Von der wiederum ausgeschiedenen geringen Kristallmenge wird abfiltriert, das Benzol abdestilliert und der Rückstand an der Hochvakuumpumpe fraktioniert. Die neue Base geht bei 165 bis i66° unter o;5 mm Druck als farbloses Öl über. Das Dihydrobromid, erhalten durch Versetzen der Base mit Bromwasserstoffsäure in Äther, stellt ein hygroskopisches, weißes Salz dar. Es enthält 36,1'1, Br (berechnet 36,8 0jo Br). Beispiel 2 i-Phenyl-2-(dimethylaminobutylmethyl) -aminopropan-i-ol 13,59 i-Dimethylamino-3-chlorbutan werden mit 33 g Ephedrinbase im geschlossenen Gefäß etwa 24 Stunden im Wasserbad erwärmt. Es scheidet sich salzsaures Ephedrin ab, welches nach dem Verreiben mit Äther abgesaugt wird. Die Lösung wird vom Äther befreit und der Rückstand im Hochvakuum destilliert. Die neue Base geht als dickes Öl vom Kpo,s 165 bis 168° über. Die Base wird mit der berechneten Menge Phosphorsäure in Methanol neutralisiert und die Lösung eingeengt. Beim Versetzen mit Äther scheidet sich das phosphorsaure Salz ab. Es enthält 13,7 0fo P (berechnet 13,5 0/0) und stellt ein hygroskopisches, farbloses Salz dar.The new compounds are said to be used for therapeutic purposes or as intermediates serve to manufacture new remedies. Example i-phenyl-2- (methyl- [diethylamine @ propyl] ) -aminopropan-i-ol 33o parts of ephedrine are dissolved in i 5 5 parts of benzene and mixed with 150 parts of i-diethylamino-3-chloropropane (C2 H5) 2 # N # CH. # CH2 # CH2 # Cl offset. The solution is refluxed for 10 hours, during which a crystal slurry of hydrochloric acid ephedrine separates. This is separated off and the filtrate to complete the reaction heated for 3 hours in a closed vessel in a boiling water bath. The benzene is filtered off from the small amount of crystals that have separated out distilled off and the residue fractionated on the high vacuum pump. The new base goes at 165 to i66 ° under o; 5 mm pressure as a colorless oil over. The dihydrobromide obtained by adding hydrobromic acid to the base in Ether, is a hygroscopic, white salt. It contains 36,1'1, Br (calculated 36.8 0jo Br). Example 2 i-Phenyl-2- (dimethylaminobutylmethyl) aminopropan-i-ol 13.59 i-Dimethylamino-3-chlorobutane are mixed with 33 g of ephedrine base in the closed The vessel is warmed in a water bath for about 24 hours. Hydrochloric acid ephedrine separates which is sucked off after rubbing with ether. The solution comes from the ether freed and the residue distilled in a high vacuum. The new base goes as a thick one Oil from the Kpo, s 165 to 168 ° above. The base is with the calculated amount of phosphoric acid neutralized in methanol and the solution concentrated. When displacing with ether separates the phosphoric acid salt. It contains 13.7 0fo P (calculated 13.5 0/0) and represents is a hygroscopic, colorless salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Diaminoalkoholen der aromatischen Reihe, dadurch gekennzeichnet, daß man in Abänderung des Verfahrens nach Patent 611 5o i das i-Phenyl-2-methylaminopropan-i-ol statt mit Halogeniden oder Sulfonsäureestern von Dialkylaminoäthanolen oder den Salzen dieser Verbindungen hier mit Halogeniden oder Sulfonsäureestern von anderen Dialkylaminoalkoholen oder den Salzen dieser Verbindungen umsetzt. PATENT CLAIM: Process for the preparation of diamino alcohols of the aromatic series, characterized in that the i-phenyl-2-methylaminopropan-i-ol instead of halides or sulfonic acid esters of dialkylaminoethanols or the salts of these compounds is used here as a modification of the process according to patent 611 501 with halides or sulfonic acid esters of other dialkylamino alcohols or the salts of these compounds.
DEC48932D 1934-03-03 1934-03-03 Process for the preparation of diamino alcohols of the aromatic series Expired DE619756C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC48932D DE619756C (en) 1934-03-03 1934-03-03 Process for the preparation of diamino alcohols of the aromatic series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC48932D DE619756C (en) 1934-03-03 1934-03-03 Process for the preparation of diamino alcohols of the aromatic series

Publications (1)

Publication Number Publication Date
DE619756C true DE619756C (en) 1935-10-05

Family

ID=7026862

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC48932D Expired DE619756C (en) 1934-03-03 1934-03-03 Process for the preparation of diamino alcohols of the aromatic series

Country Status (1)

Country Link
DE (1) DE619756C (en)

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