CH245894A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245894A
CH245894A CH245894DA CH245894A CH 245894 A CH245894 A CH 245894A CH 245894D A CH245894D A CH 245894DA CH 245894 A CH245894 A CH 245894A
Authority
CH
Switzerland
Prior art keywords
imidazoline
oxy
phenyl
hydrochloride
preparation
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 CH245894A publication Critical patent/CH245894A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

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

Description

  

  Verfahren zur Herstellung eines neuen     Imidazolins.            Gegenstand    .des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    eines neuen       Imidazolins,    das dadurch gekennzeichnet ist,  dass man einen reaktionsfähigen Ester des       2-Oxymethyl-imidazolins        bezw.        ein    Salz die  ses Esters mit     N-(3-Oxy-phenyl)-benzylamin     umsetzt.  



  Das so erhaltene     2-[N-(3'-Oxy-phenyl)-N-          benzyl-aminomethyl]        -imidazolin    bildet ein       Hydrochlorid    in     Form    von farblosen Kristal  len, die bei 227 bis 228  schmelzen. Es soll  pharmazeutische Verwendung finden oder als  Zwischenprodukt zur Herstellung von Heil  mitteln dienen.  



  Als     reaktionsfähiger        Ester    des     2-Ogy-          methyl-imidazolins    wird insbesondere ein sol  cher mit einer starken anorganischen oder  organischen Säure, wie z. B. einer Halogen  wasserstoffsäure     sowie    einer     Alkyl-    oder       Arylsulfonsäure,    und vorzugsweise     in    Form  eines seiner Salze verwendet. Die Umsetzung  kann in An- oder Abwesenheit von Verdün  nungsmitteln und/oder Kondensationsmitteln  durchgeführt werden.

           Beispiel:     15,5 Teile 2 -     Chlormethyl    -     imidazolin-          hydrochlorid,    47,7 Teile     N-(3-Oxy-phenyl)-          benzylamin    und 50 Teile Alkohol werden  während einigen     Stunden    auf 90 bis 105  in  einem Ölbad     erhitzt.    Sodann wird der Al  kohol     abdestilliert    und der Rückstand mit  einer     wässrigen    Lösung von 8,4     Teilen        Na-          triumbicarbonat    oder mit der entsprechenden  Menge     Ammoniak    verrieben.

   Das     unver-          brauchte        N-(3-Oxy-phenyl)-benzylamin    wird  mit einem     Lösungsmittel,    wie Äther, Benzol  oder     Toluol,    ausgezogen, die     wässrige    Schicht  mit wenig verdünnter Salzsäure     neutralisiert     und zum Sieden erhitzt.

   Beim Abkühlen der       Lösung    fällt das 2-     [N-(3'-Oxy-phenyl)-N-          benzyl    -     aminomethyl]    -     imidazolin    -     hydro-          chlorid    in Form farbloser Kristalle vom  F. 227 bis 228      aus.     



  An Stelle von     Chlormethyl-imidazolin-          hydrochlorid        kann    man von einem     andern     reaktionsfähigen     Ester    des 2 -     Oxymethyl-          imidazolins,    wie z. B. vom Bromwasserstoff  säure- oder     Toluolsulfosäureester,    ausgehen.      Ebenso     lässt    sich an Stelle des     Hydrochlorids     ein anderes Salz oder die freie Base ver  wenden. -



  Process for the preparation of a new imidazoline. The subject of the present patent is a process for the preparation of a new imidazoline, which is characterized in that a reactive ester of 2-oxymethylimidazoline or a salt that reacts this ester with N- (3-oxy-phenyl) -benzylamine.



  The 2- [N- (3'-oxy-phenyl) -N-benzyl-aminomethyl] -imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 227-228. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products.



  As a reactive ester of 2-Ogy- methyl-imidazoline in particular a sol cher with a strong inorganic or organic acid, such as. B. a halogenated hydrochloric acid and an alkyl or aryl sulfonic acid, and preferably used in the form of one of its salts. The reaction can be carried out in the presence or absence of diluents and / or condensing agents.

           Example: 15.5 parts of 2-chloromethyl-imidazoline hydrochloride, 47.7 parts of N- (3-oxy-phenyl) -benzylamine and 50 parts of alcohol are heated to 90-105 in an oil bath for a few hours. The alcohol is then distilled off and the residue is triturated with an aqueous solution of 8.4 parts of sodium bicarbonate or with the appropriate amount of ammonia.

   The unused N- (3-oxy-phenyl) -benzylamine is extracted with a solvent such as ether, benzene or toluene, the aqueous layer is neutralized with a little dilute hydrochloric acid and heated to the boil.

   When the solution cools, the 2- [N- (3'-oxy-phenyl) -N-benzyl-aminomethyl] -imidazoline hydrochloride precipitates in the form of colorless crystals with a melting point of 227 to 228.



  Instead of chloromethyl imidazoline hydrochloride one can use another reactive ester of 2 - oxymethyl imidazoline, such as. B. from the hydrobromic acid or toluenesulfonic acid ester, proceed. Another salt or the free base can also be used instead of the hydrochloride. -

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Imidazolins, dadurch gekennzeichnet, dass man einen reaktionsfähigen Ester des 2-Oxy- methyl-imidazolins bezw. ein Salz dieses Esters mit N-(8-Oxy-phenyl)-benzylamin umsetzt. Das so erhaltene 2-[N-(8'-Oxy-phenyl)-N- benzyl-aminomethyl] -imidazalin bildet ein Hydrochlorid in Form von farblosen Kristal len, die bei 227 bis 228 schmelzen. PATENT CLAIM: Process for the production of a new imidazoline, characterized in that a reactive ester of 2-oxymethyl-imidazoline or a salt of this ester is reacted with N- (8-oxy-phenyl) -benzylamine. The 2- [N- (8'-oxy-phenyl) -N-benzyl-aminomethyl] -imidazalin obtained in this way forms a hydrochloride in the form of colorless crystals, which melt at 227-228. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Herstellung von Heil mitteln dienen. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, .da durch gekennzeichnet, dass man ein Salzeines 2-Halogenmethyl-imidazolins als Ausgangs stoff verwendet. 2.. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 2-Chlor- methyl - imidazolin - hydrochlorid als Aus gangsstoff verwendet. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products. SUBClaims: 1. The method according to claim, .da characterized in that a salt of a 2-halomethyl-imidazoline is used as the starting material. 2. The method according to claim, characterized in that 2-chloromethyl - imidazoline - hydrochloride is used as the starting material.
CH245894D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245894A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242839T 1944-03-23
CH245894T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245894A true CH245894A (en) 1946-11-30

Family

ID=25728742

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245894D CH245894A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245894A (en)

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