CH245897A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245897A
CH245897A CH245897DA CH245897A CH 245897 A CH245897 A CH 245897A CH 245897D A CH245897D A CH 245897DA CH 245897 A CH245897 A CH 245897A
Authority
CH
Switzerland
Prior art keywords
imidazoline
phenyl
hydrochloride
preparation
methoxy
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 CH245897A publication Critical patent/CH245897A/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

  

      Türfahren    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-Oxym-ethyl-imidazolins        bezw.    ein Salz die  ses     Esters    mit     N-Phenyl-4-methoxy-benzyl-          amin    umsetzt.  



  Das so erhaltene     2-[N-Phenyl-N-(4'-          methoxy    -     benzyl)    -     aminomethyll    -     imidazolin     bildet ein Hydrochlorid in Form von farb  losen Kristallen, die bei 211 bis 212  schmel  zen. Es soll     pharmazeutische    Verwendung  finden oder     als        Zwischenprodukt    zur Her  stellung 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  wasserstoffsäure     sowie    einer     Alkyl-    oder       Ary1sulfonsäure,    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>  15,5 Teile 2 -     Chlormethyl    -     imidazolin-          hydrochlorid,    50 Teile     N-Phenyl-4-methoxy-          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-Phenyl-4-methogy-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-Phenyl-N-          (4'    -     methogy    -     benzyl)    -     aminomethyl]    -     imid-          azolin-hydrochlorid    in Form     farbloser    Kri  stalle vom F. 211 bis     212     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.



      Door travel to manufacture a new imidazoline. The subject matter of the present patent is a process for the preparation of a new imidazoline, which is characterized in that a reactive ester of 2-oxymethyl-imidazoline is respectively. a salt this ester reacts with N-phenyl-4-methoxy-benzylamine.



  The 2- [N-phenyl-N- (4'-methoxy - benzyl) - aminomethyll - imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals that melt at 211 to 212. It should find pharmaceutical use or serve as an intermediate for 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 halogenated hydrochloric acid and an alkyl or Ary1sulfonsäure, 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.

      <I> Example: </I> 15.5 parts of 2 - chloromethyl - imidazoline hydrochloride, 50 parts of N-phenyl-4-methoxy-benzylamine and. 50 parts of alcohol are used during. Heated for a few hours to 90 to 105 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-phenyl-4-methogy-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-phenyl-N- (4 '- methogy - benzyl) - aminomethyl] - imidazoline hydrochloride precipitates in the form of colorless crystals with a melting point of 211 to 212.



  Instead of chloromethyl - imidazoline hydrochloride, you 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-Phenyl-4-methoxy-benzylamin 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 reacts with N-phenyl-4-methoxy-benzylamine. Das so erhaltene 2 - [N - Phenyl - N - ( _4' methoxy - benzyl) - aminomethyl] - imidazolin bildet ein Hydrochlorid in Form von farb losen Kristallen, die bei 211 bis 212 schmel- zen. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Her stellung von Heilmitteln .dienen. UNTTERANSPRüCHE: 1. The 2 - [N - phenyl - N - (_4 'methoxy - benzyl) - aminomethyl] - imidazoline thus obtained forms a hydrochloride in the form of colorless crystals, which melt at 211 to 212. It should be used in pharmaceuticals or as an intermediate for the manufacture of medicinal products. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Salz eines 2 -Halo <B>9</B> enmethyl-imidazolins als Ausgangs- stoff verwendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 2-Chlor- methyl - imidazolin - hydrochlorid als Aus gangsstoff verwendet. Process according to patent claim, characterized in that a salt of a 2-halo 9 enmethyl imidazoline is used as the starting material. 2. The method according to claim, characterized in that 2-chloro-methyl - imidazoline - hydrochloride is used as the starting material.
CH245897D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245897A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH245897T 1944-03-23
CH242839T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245897A true CH245897A (en) 1946-11-30

Family

ID=25728745

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245897D CH245897A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245897A (en)

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