DE615412C - Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol - Google Patents

Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol

Info

Publication number
DE615412C
DE615412C DEC47478D DEC0047478D DE615412C DE 615412 C DE615412 C DE 615412C DE C47478 D DEC47478 D DE C47478D DE C0047478 D DEC0047478 D DE C0047478D DE 615412 C DE615412 C DE 615412C
Authority
DE
Germany
Prior art keywords
phenyl
aminopropan
preparation
diethylaminoethyl
diaethylaminoaethyl
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
DEC47478D
Other languages
German (de)
Inventor
Dr Gustav Heilner
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 DEC47478D priority Critical patent/DE615412C/en
Application granted granted Critical
Publication of DE615412C publication Critical patent/DE615412C/en
Expired legal-status Critical Current

Links

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

Landscapes

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

Description

Verfahren zur Herstellung von 1-Phenyl-2-(diäthylaminoäthyl)-aminopropan-l-ol Durch -las Patent 611 5oi ist die Herstellung von Diaminoalkoholen der aromatischen Reihe geschützt, welche sich vom Phenylmethylaminopropanol herleiten und somit ditertiäre Aminoalkohole darstellen.Process for the preparation of 1-phenyl-2- (diethylaminoethyl) aminopropan-l-ol By -las patent 611 5oi is the production of diamino alcohols of the aromatic Protected series, which are derived from Phenylmethylaminopropanol and thus ditertiary Represent amino alcohols.

Gegenstand vorliegender Erfindung ist ein Verfahren zur Gewinnung eines Diaminoalkohols, welcher sich vom Phenvlaminopropanol herleitet und als sekundär-tertiärer Aminoalkohol anzusehen ist.The present invention relates to a method of extraction a diamino alcohol, which is derived from phenylaminopropanol and as a secondary-tertiary Amino alcohol is to be considered.

Es wurde gefunden, daß man durch Behandeln von i-Phenyl-2-aminopropan-i-ol mit Diäthylaminoäthylhalogeniden oder den entsprechenden Sulfonsäureestern oder-den Salzen dieser Verbindungen zu dem bisher noch nichtbeschriebenen i-Phenyl-2-(diäthyl`äminoäthyl)-aminopropan-i-ol gelangt. Die Umsetzung kann sowohl bei Gegenwart -wie auch bei Abwesenheit von säurebindenden Mitteln durchgeführt werden.It has been found that by treating i-phenyl-2-aminopropan-i-ol with diethylaminoethyl halides or the corresponding sulfonic acid esters or the Salts of these compounds to give i-phenyl-2- (diethyl`äminoäthyl) aminopropan-i-ol, which has not yet been described got. The reaction can be carried out either in the presence or in the absence of acid-binding agents Funds are carried out.

Das i-Phenyl-2-(diäthylaminoäthyl)-aminopropan-i-ol stellt ein im Vakuum unzersetzt destillierbares Öl dar, welches ein gut kristallisiertes diprimäres Phosphat und Dihydrojodid bildet. Es soll therapeutisch verwendet werden, da es die Bronchien in demselben Umfang wie Phenylmethy laminopropanol erweitert, in Gegensatz zu letzterem aber den Blutdruck unbeeinflußt läßt und die Atmung verbessert. Beispiel i-Phenyl-2-(diäthylaminoäthyl)-aminopröpan-i-ol 187 g i-Phenyl-a-aminopropan-i-olhydrochlorid, 325 g des salzsauren Salzes des Toluolsulfonsäureesters des Diäthylaminoäthanols, iooo g Benzol und 165 g Kaliumhydrokyd, in i l Wasser gelöst, werden unter gutem Rühren einige Stunden unter Rückfluß erhitzt. Hierauf wird die Benzolschicht abgehoben, das Benzol unter vermindertem Druck abdestilliert und der Rückstand der Vakuumdestillation bei hohem Vakuum unterworfen. Die neue Verbindung siedet bei ungefähr o,5 mm bei etwa i40°. Das Dihydrojodid schmilzt bei iez bis i83' unter Zersetzung.The i-phenyl-2- (diethylaminoethyl) aminopropan-i-ol is an im Vacuum undecomposed distillable oil, which is a well crystallized diprimary Forms phosphate and dihydroiodide. It is meant to be used therapeutically as it is the bronchi dilated to the same extent as phenylmethy laminopropanol, in contrast for the latter, however, it leaves the blood pressure unaffected and improves breathing. example i-phenyl-2- (diethylaminoethyl) -aminoproepan-i-ol 187 g of i-phenyl-a-aminopropan-i-ol hydrochloride, 325 g of the hydrochloric acid salt of the toluenesulfonic acid ester of diethylaminoethanol, 100 g of benzene and 165 g of potassium hydroxide, dissolved in one liter of water, are mixed in with a good amount of water Stir under reflux for a few hours. Then the benzene layer is lifted off, the benzene is distilled off under reduced pressure and the residue from vacuum distillation subjected to high vacuum. The new compound boils at about 0.5 mm about i40 °. The dihydroiodide melts at iez to 183 'with decomposition.

Claims (1)

PATENTANSPRÜCHE: i. Weitere Ausbildung des Verfahrens gemäß Patent 611 5o-i, dadurch gekennzeichnet, daß man hier zwecks Herstellung von i-Phenyl-z-(diäthylaminoäthyl) - aminopropan - i - o1 i - Phenyla-aminopropan-i-ol mit Diäthylaminoäthylhalogeniden oder den entsprechenden Sulfonsäureestern oder deren Salzen behandelt. z. Verfahren nach Anspruch i, darin bestehend, daß man die Umsetzung bei Gegenwart von säurebindenden Mitteln durchführt. PATENT CLAIMS: i. Further development of the process according to patent 611 5o-i, characterized in that here for the purpose of preparing i-phenyl-z- (diethylaminoethyl) - aminopropane - i - o1 i - phenyla-aminopropan-i-ol with diethylaminoethyl halides or the corresponding sulfonic acid esters or their salts treated. z. Process according to claim i, comprising carrying out the reaction in the presence of acid-binding agents.
DEC47478D 1933-02-02 1933-02-02 Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol Expired DE615412C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC47478D DE615412C (en) 1933-02-02 1933-02-02 Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC47478D DE615412C (en) 1933-02-02 1933-02-02 Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol

Publications (1)

Publication Number Publication Date
DE615412C true DE615412C (en) 1935-07-03

Family

ID=7026569

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC47478D Expired DE615412C (en) 1933-02-02 1933-02-02 Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol

Country Status (1)

Country Link
DE (1) DE615412C (en)

Similar Documents

Publication Publication Date Title
DE2061838A1 (en) 2-Phosphono-butane-1,2-dicarboxylic acid derivatives, process for their preparation and their use as complexing agents
DE615412C (en) Process for the preparation of 1-phenyl-2- (diaethylaminoaethyl) aminopropan-1-ol
DE2528895B2 (en) Process for the preparation of low-vanadium alkali metal phosphate solutions
DE3240687A1 (en) AGENT FOR REDUCING LIQUID ADHESIVES ON METALLIC SURFACES
DE696779C (en) Process for the production of tetrahydrofurans
DE816701C (en) Process for the production of phosphorus-containing derivatives of m-dimethylaminophenol
DE885753C (en) Process for the production of an electrolyte, in particular for electrolytic capacitors
DE611501C (en) Process for the preparation of clusters of optically active or racemic 1-phenyl-2-methylaminopropan-1-ol
DE843415C (en) Process for the preparation of a guaiacol derivative
DE658389C (en) Process for the preparation of water-soluble salts giving benzoic acid esters
DE665368C (en) Process for the preparation of alkylenes
DE646932C (en) Process for the production of diamino alcohols of the fatty aromatic series
DE625590C (en) Process for the preparation of an arylamino alcohol
DE883883C (en) Method of treating wool
DE619756C (en) Process for the preparation of diamino alcohols of the aromatic series
DE585519C (en) Process for the preparation of organic bismuth compounds
DE615638C (en) Process for the preparation of organic bismuth compounds
AT92388B (en) Process for the preparation of aralkyl esters of benzylamine carboxylic acids.
DE616119C (en) Process for the preparation of 2,4-diaminoazobenzene compounds
DE248255C (en)
DE396507C (en) Process for the preparation of pyrazolone derivatives
DE667844C (en) Process for the preparation of amino-substituted arsenobenzene-formaldehyde bisulfite compounds
DE665792C (en) Process for the production of Diaethylaminoaethanol
DE582715C (en) Process for the preparation of 4-butylaminobenzoic acid ª ‰ -dimethylaminoaethyl ester
CH174279A (en) Process for the preparation of phenylbromoallylacetic acid 2,2-dimethyl-3-diethylaminopropanol ester.