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CH245889A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245889A
CH245889A CH245889DA CH245889A CH 245889 A CH245889 A CH 245889A CH 245889D A CH245889D A CH 245889DA CH 245889 A CH245889 A CH 245889A
Authority
CH
Switzerland
Prior art keywords
imidazoline
hydrochloride
preparation
salt
ester
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 CH245889A publication Critical patent/CH245889A/en

Links

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)
  • 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-Ogymethyl-imidazolins        bezw.    ein Salz die  ses Esters mit     N-(4-Methogy-phenyl)-benzyl-          amin    umsetzt.  



  Das so erhaltene 2-     [N-    (4'-     Methogy-          phenyl)    - N -     benzyl    -     aminamethyl]        -imidazolin     bildet ein Hydrochlorid in Form von farb  losen Kristallen, die bei 206 bis 208  schmel  zen. Es soll pharmazeutische Verwendung  finden oder als Zwischenprodukt zur Herstel  lung von     Heilmitteln    dienen.  



  Als reaktionsfähiger Ester     des        2-Ogy-          methyl-imidazolins    wird insbesondere ein  solcher mit einer starken anorganischen oder  organischen Säure, wie z. B. einer     Halogen-          wasserstoffOure    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.

      <I>Beispiel:</I>  <B>15,5</B> Teile 2 -     Chlormethyl    -     imidazolin-          hydrochlorid,    50 Teile     N-(Methogy-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-     (4-Methogy-phenyl)-benzylamin          wird    mit einem     Lösungsmittel,    wie Äther;  Benzol oder     Toluol,    ausgezogen, die     wässrige     Schicht mit     wenig    verdünnter Salzsäure neu  tralisiert und zum Sieden erhitzt. Beim Ab  kühlen der Lösung fällt das 2 -     [N    -     (4'-        Me-          tliogy-phenyl)-N-benzyl-aminomethyl]        -imid-          azolin-hydrochlorid    in Form farbloser Kri  stalle vom F. 206 bis 208  aus.  



  An Stelle von     Chlormethyl-imidazolin-          hydrochlorid    kann man von einem andern  reaktionsfähigen Ester des 2 -     Ogymethyl-          imida.zolins.,    wie z. B. vom Bromwasserstoff  säure- oder     Toluolsulfosäure-ester,    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 present patent relates to a process for the preparation of a new imidazoline which is characterized by this. that a reactive ester of 2-ogymethyl-imidazoline BEZW. a salt that reacts this ester with N- (4-methogyphenyl) benzyl amine.



  The 2- [N- (4'-methogyphenyl) -N-benzyl-aminamethyl] -imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals that melt at 206-208. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products.



  The reactive ester of 2-ogymethyl-imidazoline is in particular one with a strong inorganic or organic acid, such as. B. a halogen hydrogen or 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 condensation agents.

      <I> Example: </I> <B> 15.5 </B> parts of 2 - chloromethyl - imidazoline hydrochloride, 50 parts of N- (methogyphenyl) - benzylamine and 50 parts of alcohol are reduced to 90 to 105 heated in an oil bath. 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- (4-Methogy-phenyl) -benzylamine is treated with a solvent such as ether; Benzene or toluene, extracted, the aqueous layer neutralized with a little dilute hydrochloric acid and heated to the boil. When the solution cools, the 2 - [N - (4'-Metliogy-phenyl) -N-benzyl-aminomethyl] -imidazoline hydrochloride precipitates in the form of colorless crystals with a melting point of 206 to 208.



  Instead of chloromethyl imidazoline hydrochloride one can use another reactive ester of 2 - Ogymethyl imida.zoline. B. from the hydrogen bromide 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-(4-11lethoxy-phenyl)-benzyl- amin umsetzt. 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- (4-11lethoxyphenyl) benzyl amine. Das so erhaltene 2 - [N - (4 '- AIethoxy- phenyl) -N-benzyl-aminomethyll-imidazolin bildet ein Hydrochlorid in Form von farb losen Kristallen, die bei<B>206</B> bis 208 schmel- zen. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Her stellung von Heilmitteln dienen. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Salz eines 2-Halogenmethyl-iinidazolins als Ausgangs- stoff verwendet. The 2 - [N - (4 '- Alethoxyphenyl) -N-benzyl-aminomethyll-imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 206-208. It should find pharmaceutical use or serve as an intermediate for the manufacture of medicinal products. SUBClaims: 1. Process according to claim, characterized in that a salt of a 2-halomethyl-iinidazoline is used as the starting material. \?. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ?-Chlor methyl-imidazolin-hydroclilorid als Ausgangs stoff verwendet. \ ?. Process according to patent claim, characterized in that? -Chloro methyl imidazoline hydrochloride is used as the starting material.
CH245889D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245889A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242839T 1944-03-23
CH245889T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245889A true CH245889A (en) 1946-11-30

Family

ID=25728737

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245889D CH245889A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245889A (en)

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