CH245892A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245892A
CH245892A CH245892DA CH245892A CH 245892 A CH245892 A CH 245892A CH 245892D A CH245892D A CH 245892DA CH 245892 A CH245892 A CH 245892A
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 CH245892A publication Critical patent/CH245892A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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-Ogymethyl-imidazolins        bezw.        ein    Salz die  ses     Esters    mit     N-Naphthyl-(1)-benzylamin          umsetzt.     



  Das so erhaltene     2-[N-Naphthyl-(1')-N-          benzyl-aminomethyl]-imidazoIin        bildet    ein       Hydrochlorid    in Form von farblosen Kri  stallen, die bei 207 bis 209  schmelzen. Es  soll pharmazeutische Verwendung finden  oder als Zwischenprodukt zur Herstellung  von Heilmitteln 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,   <B>56</B>     Teile    N -     Naphthyl-    (1)     -          benzylamin    und 50 Teile Alkohol werden  während einigen     Stunden    auf 90 bis 105  in  einem     Ülbad    erhitzt.

   Sodann wird der Al  kohol     abdestilliert    und der Rückstand mit  einer     wässrigen        Lösung    von 8,4 Teilen     Na-          triumbicarbonat    oder mit der entsprechen  den Menge Ammoniak verrieben. Das unver  brauchte     N-Naphthyl-(1)-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-(1')-N-ben-          zyl-aminomethyl]        -imidazolin-hydrochlorid    in  Form farbloser     Kristalle    vom F. 207 bis  209  aus.  



  An Stelle von     Chlormethyl-imidazolin-          hydrochlorid    kann man von einem andern  reaktionsfähigen Ester des 2 -     Ogymethyl-          imidazolins,    wie z. B. vom Bromwasserstoff  säure- oder     Toluoleulfosäureester,    ausgehen.           Ebenso    lässt sieh 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-ogymethyl-imidazoline or. a salt which reacts this ester with N-naphthyl- (1) -benzylamine.



  The 2- [N-naphthyl- (1 ') -N-benzyl-aminomethyl] -imidazoIin thus obtained forms a hydrochloride in the form of colorless crystals which melt at 207-209. 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, 56 parts of N-naphthyl- (1) -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 corresponding amount of ammonia. The unused N-naphthyl- (1) -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- (1 ') - N-benzyl-aminomethyl] -imidazoline hydrochloride precipitates in the form of colorless crystals with a melting point of 207 to 209.



  Instead of chloromethyl imidazoline hydrochloride one can use another reactive ester of 2 - ogymethyl imidazoline, such as. B. from the hydrobromic acid or toluenesulfonic acid ester, proceed. You can also use a different salt or the free base 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-(.1)-benzylamin um setzt. PATENT CLAIM: Process for the production of a new imidazoline, characterized in that one has a reactive ester of 2-oxymethyl - imidazoline or respectively. a salt of this ester with N-naphthyl- (. 1) -benzylamine sets. Das so erhaltene 2-[N-Naphthyl-(1')-N- benzyl-aminomethyll- imidazolin bildet ein Hydrochlorid in Form von farblosen Kri stallen, die bei 207 bis 209 schmelzen. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Herstellung von Heilmitteln dienen. UNTERAN SPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, da.ss man ein Salz eines 2-Halogenmethyl-iinidazolins als Ausgangs stoff verwendet. 2. The 2- [N-naphthyl- (1 ') - N-benzyl-aminomethyll-imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 207-209. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products. SUBJECT DISCLAIMERS 1. The method according to claim, characterized in that a salt of a 2-halomethyl-iinidazoline is used as the starting material. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man \? - Chlor methyl-imidazolin-hydrochlorid als Aus gangsstoff verwendet. Method according to claim, characterized in that one \? - Chlorine methyl imidazoline hydrochloride used as a starting material.
CH245892D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245892A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242839T 1944-03-23
CH245892T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245892A true CH245892A (en) 1946-11-30

Family

ID=25728740

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245892D CH245892A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245892A (en)

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