CH245896A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245896A
CH245896A CH245896DA CH245896A CH 245896 A CH245896 A CH 245896A CH 245896D A CH245896D A CH 245896DA CH 245896 A CH245896 A CH 245896A
Authority
CH
Switzerland
Prior art keywords
imidazoline
naphthyl
hydrochloride
preparation
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 CH245896A publication Critical patent/CH245896A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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-Naphthyl-(2)-benzylamin     umsetzt.  



  Das so erhaltene     2-[N-Naphthyl-(2')-N-          benzyl-aminomethyl]        -imidazolin    bildet     ein          Hydrochlorid    in Form von farblosen Kristal  len, die bei<B>231</B> bis 232  schmelzen. Es soll  pharmazeutische Verwendung finden oder  als Zwischenprodukt zur Herstellung von  Heilmitteln dienen.  



  Als reaktionsfähiger Ester des     2-Oxy-          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     'aer    Salze verwendet. Die     Umsetzung     kann     L..    An- oder     Abwesenheit    von Verdün  nungsmitteln     und/oder        Kondensationsmitteln     durchgeführt werden.

           Beispiel:     15,5 Teile 2 -     Chlormethyl    -     imidazolin-          hydrochlorid,    56 Teile     N-Naphthyl-(2)-ben-          zylamin    und 50 Teile Alkohol werden wäh  rend einigen Stunden auf 90 bis 105      in    einem  Ölbad erhitzt.

   Sodann wird der Alkohol ab  destilliert und der     Rückstand    mit einer     wäss-          rigen    Lösung von 8,4 Teilen     Natriumbicar-          bongt    oder mit der entsprechenden Menge  Ammoniak     verrieben.    Das unverbrauchte N  Naphthyl-(2)-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-Naphthyl-(2')-N-benzyl-amino-          methyll    -     imidazolin    -     hydrochlorid    in Form  farbloser     Kristalle    vom F. 231 bis 232  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     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 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-oxymethyl-imidazoline or. a salt which reacts this ester with N-naphthyl- (2) -benzylamine.



  The 2- [N-naphthyl- (2 ') - N-benzyl-aminomethyl] -imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 231 to 232. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products.



  The reactive ester of 2-oxymethyl-imidazoline is 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 an 'aer salts. The reaction can be carried out L .. presence or absence of diluents and / or condensation agents.

           Example: 15.5 parts of 2-chloromethyl-imidazoline hydrochloride, 56 parts of N-naphthyl- (2) -benzylamine and 50 parts of alcohol are heated in an oil bath to 90-105 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 naphthyl- (2) -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-naphthyl- (2 ') - N-benzyl-aminomethyll - imidazoline - hydrochloride precipitates in the form of colorless crystals with a melting point of 231 to 232.



  Instead of chloromethyl imidazoline hydrochloride one can use another reactive ester of 2 - oxymethyl imidazoline, such as. 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, da,ss man einen reaktionsfähigen Ester des 2-Oxy- methyl-imidazolins bezw. ein Salz dieses Esters mit N-Naphthyl-(2)-benzylamin um setzt. PATENT CLAIM: Process for the production of a new imidazoline, characterized in that one ss a reactive ester of 2-oxymethyl-imidazoline respectively. a salt of this ester with N-naphthyl- (2) -benzylamine sets. Das so erhaltene 2-[N-Naphthyl-(2\)-N- benzyl-aminomethyl]-imidazolin bildet ein Hydrochlorid in Form von farblosen Kristal len, die bei 231 bis 232 schmelzen. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Herstellung von Heilmitteln dienen. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Salzeines 2-Halogenmethyl-imidazolins als Ausgangs stoff verwendet. 2. The 2- [N-naphthyl- (2 \) - N-benzyl-aminomethyl] -imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 231-232. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products. SUBClaims: 1. Method according to patent claim, characterized in that a salt of a 2-halomethyl imidazoline is used as the starting material. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass mann ein 2-Chlor- methyl-imidazolin-hydrochlorid als Ausgangs stoff verwendet. Process according to patent claim, characterized in that a 2-chloromethyl-imidazoline hydrochloride is used as the starting material.
CH245896D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245896A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242839T 1944-03-23
CH245896T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245896A true CH245896A (en) 1946-11-30

Family

ID=25728744

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245896D CH245896A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245896A (en)

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