CH293627A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

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Publication number
CH293627A
CH293627A CH293627DA CH293627A CH 293627 A CH293627 A CH 293627A CH 293627D A CH293627D A CH 293627DA CH 293627 A CH293627 A CH 293627A
Authority
CH
Switzerland
Prior art keywords
imidazoline
new
preparation
phenyl
methyl
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH293627A publication Critical patent/CH293627A/en

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Description

  

  Verfahren zur Herstellung     eines    neuen     Imidazolins.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Imidazolins,    welches dadurch gekennzeichnet  ist, dass man in einer Verbindung der Formel  
EMI0001.0004     
    worin R einen durch Hydrolyse in eine     Oxy-          gruppe        überführbaren    Rest bedeutet, diesen  durch     13ydrolyse    in eine solche überführt.  



       Da\s    erhaltene     2-[N-(p-1Vlethyl-phenyl)-N-          (m'-oxy-phenyl)-amino-methyl]-imidazolin    ist  neu. Es schmilzt bei 174 bis 175  und bildet  leicht Salze mit anorganischen oder organi  schen Säuren, z. B. mit     Halogenwasserstoff-          säure,    wie der Salzsäure, mit Schwefelsäure,  Phosphorsäure,     Methansulfosäure    oder     Toluol-          sulfosäure,    Essigsäure und dergleichen, so z. B.  ein salzsaures Salz vom Schmelzpunkt 239 bis  240 .  



  Das neue     Imidazolin    zeigt     sympathicoly-          tische    Wirkung und soll als Heilmittel Ver  wendung finden.  



  <I>Beispiel:</I>  50 Teile 2-[N-     (p-Methyl-phenyl)-N-(m'-          methoxy-phenyl)        -amino-methyl]-imidazolin-          hydrochlorid    (hergestellt aus     N-(p-Methyl-          phenyl)-m'-methoxy-phenyl-amin    und     2-Chlor-          methyl-imidazolin-hydrochlorid)    werden in    300 Teilen     o-Dichlorbenzol    suspendiert und in  einem Strom von trockenem     Salzsäuregas    wäh  rend 10 Stunden auf 150  erhitzt. Nach dem  Erkalten wird das Lösungsmittel von dem  harten Rückstand abgegossen und dieser aus       Alkohol-Essigester    kristallisiert.

   Das erhal  tene     2-[N-(p-Methyl-phenyl)-N-(m'-oxy-phe-          nyl)    -     amino        -methyl    ] -     imidazolin-        hydrochlorid     schmilzt bei 239 bis 240 . Aus seiner wässeri  gen Lösung kann mit verdünntem Ammoniak  die Base freigesetzt werden. Sie schmilzt bei  1.74 bis 175  und hat die Formel  
EMI0001.0037     




  Process for the preparation of a new imidazoline. The present patent relates to a process for the preparation of a new imidazoline, which is characterized in that in a compound of the formula
EMI0001.0004
    where R denotes a radical which can be converted into an oxy group by hydrolysis, this group is converted into one by hydrolysis.



       The 2- [N- (p-1Vlethyl-phenyl) -N- (m'-oxy-phenyl) -amino-methyl] -imidazoline obtained is new. It melts at 174 to 175 and easily forms salts with inorganic or organic acids rule, e.g. B. with hydrohalic acid, such as hydrochloric acid, with sulfuric acid, phosphoric acid, methanesulfonic acid or toluenesulfonic acid, acetic acid and the like, for example. B. a hydrochloric acid salt with a melting point of 239 to 240.



  The new imidazoline has a sympathetic effect and is said to be used as a remedy.



  <I> Example: </I> 50 parts of 2- [N- (p-methyl-phenyl) -N- (m'-methoxyphenyl) -amino-methyl] -imidazoline hydrochloride (made from N- (p -Methyl-phenyl) -m'-methoxyphenyl-amine and 2-chloro-methyl-imidazoline hydrochloride) are suspended in 300 parts of o-dichlorobenzene and heated to 150 in a stream of dry hydrochloric acid gas for 10 hours. After cooling, the solvent is poured off from the hard residue and this is crystallized from alcohol / ethyl acetate.

   The obtained 2- [N- (p-methyl-phenyl) -N- (m'-oxy-phenyl) -amino-methyl] -imidazoline hydrochloride melts at 239 to 240. The base can be released from its aqueous solution with dilute ammonia. It melts at 1.74 to 175 and has the formula
EMI0001.0037

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Imidazolins, dadurch gekennzeichnet, dass man in einer Verbindung der Formel EMI0001.0039 worin R einen durch Hydrolyse in eine Oxy- gruppe überführbaren Rest bedeutet, diesen durch Hydrolyse in eine solche überführt. Das so erhaltene 2-[?\T-(p-iMethyl-phenyl)- N-(m'-oxy-phenyl)-amino -methyl] -imidazolin ist neu. Es schmilzt bei 174 bis 175 und bil- det ein salzsaures Salz vom Schmelzpunkt 239 bis 240 . PATENT CLAIM: Process for the preparation of a new imidazoline, characterized in that a compound of the formula EMI0001.0039 where R denotes a radical which can be converted into an oxy group by hydrolysis, this group is converted into one by hydrolysis. The 2 - [? \ T- (p-iMethyl-phenyl) -N- (m'-oxy-phenyl) -amino-methyl] -imidazoline obtained in this way is new. It melts at 174 to 175 and forms a hydrochloric acid salt with a melting point of 239 to 240. Das neue Imidazolin zeigt sympathicoly- tische WirXung und soll als Heilmittel ver wendet werden. The new imidazoline has a sympathicolytic effect and is said to be used as a remedy.
CH293627D 1947-01-31 1947-01-31 Process for the preparation of a new imidazoline. CH293627A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH283586T 1947-01-31
CH293627T 1947-01-31

Publications (1)

Publication Number Publication Date
CH293627A true CH293627A (en) 1953-09-30

Family

ID=25732264

Family Applications (1)

Application Number Title Priority Date Filing Date
CH293627D CH293627A (en) 1947-01-31 1947-01-31 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH293627A (en)

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