CH245895A - Process for the preparation of a new imidazoline. - Google Patents

Process for the preparation of a new imidazoline.

Info

Publication number
CH245895A
CH245895A CH245895DA CH245895A CH 245895 A CH245895 A CH 245895A CH 245895D A CH245895D A CH 245895DA CH 245895 A CH245895 A CH 245895A
Authority
CH
Switzerland
Prior art keywords
imidazoline
phenoxyphenyl
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 CH245895A publication Critical patent/CH245895A/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)
  • 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, dass  man einen reaktionsfähigen Ester des     2-Oxy-          methyl-imidazolins        bezw.    ein Salz dieses  Esters mit     N-(4-Phenoxy-phenyl)-benzylamin     umsetzt.  



  Das so erhaltene     2-[N-(4'-Phenoxy-          phenyl)-N-benzyl-aminomethyl]        -imidazolin     bildet ein Hydrochlorid in Form von farb  losen Kristallen, -die bei 211     bis        213     schmel  zen. Es soll pharmazeutische Verwendung  finden oder als Zwischenprodukt zur Her  stellung 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 seiner Salze verwendet. Die Umset  zung kann in An- oder Abwesenheit von Ver  dünnungsmitteln und/oder Kondensations  mitteln durchgeführt werden.

           Beispiel:     <B>15,5</B>     Teile    2 -     Chlormethyl    -     imidazolin-          hydrochlo#rid,    69 Teile N - (4 -     Phenoxy-          phenyl)-benzylamin    und 50 Teile Alkohol  werden während einigen Stunden auf 90 bis  105  in einem     Ölbad    erhitzt. Sodann wird  der Alkohol     abdestilliert    und der Rückstand  mit einer     wässrigen    Lösung von 8,4 Teilen       Natriumbicarbonat    oder mit der entsprechen  den Menge Ammoniak verrieben.

   Das un  verbrauchte     N-(4-Phenoxy-phenyl)-benzyl-          amin    wird mit einem Lösungsmittel, wie  Äther, Benzol oder     Toluol,    ausgezogen, die       wässrige    Schicht mit wenig verdünnter Salz  säure     neuträlisiert    und zum Sieden erhitzt.

    Beim Abkühlen der Lösung fällt das     2-[N-          (4'    -     Phenoxy    -     phenyl)    - N -     benzyl    -     amina-          methyl]    -     imidazolin    -     hydrochlorid    in Form  farbloser Kristalle vom F. 211 bis 213  aus.  



  An Stelle von     Chlormethyl    -     imidazo:lin-          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 matter of the present patent is a process for the production of a new imidazoline, characterized in that a reactive ester of 2-oxymethyl-imidazoline is used. a salt of this ester is reacted with N- (4-phenoxyphenyl) benzylamine.



  The 2- [N- (4'-phenoxyphenyl) -N-benzyl-aminomethyl] -imidazoline thus obtained forms a hydrochloride in the form of colorless crystals which melt at 211 to 213. It should find pharmaceutical use or serve as an intermediate for the manufacture of medicinal products.



  As a 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 one of its salts. The implementation can be carried out in the presence or absence of diluents and / or condensation agents.

           Example: 15.5 parts of 2-chloromethyl-imidazoline hydrochloride, 69 parts of N- (4-phenoxyphenyl) -benzylamine and 50 parts of alcohol are heated to 90 to 105 in one over a few hours Heated 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 corresponding amount of ammonia.

   The unused N- (4-phenoxyphenyl) -benzyl- amine 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- (4 '- phenoxyphenyl) - N - benzyl - aminamethyl] - imidazoline hydrochloride precipitates in the form of colorless crystals with a melting point of 211 to 213.



  Instead of chloromethyl - imidazo: lin 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-(4-Phenoxy-phenyl)-benzylamin umsetzt. PATENT CLAIM: A process for the production of a new imidazoline, characterized in that a reactive ester of 2-oxymethyl-imidazoline is used, respectively. a salt of this ester is reacted with N- (4-phenoxyphenyl) benzylamine. Das so erhaltene 2 - [N - (4'- Phenoxy- phenyl)-N-benzyl-aminomethyl] -imidazolin bildet ein Hydrochlorid in Form von farb losen Kristallen, die bei 211 bis 213 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-imidazolins als Ausgangs stoff verwendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 2 - Chlor methyl-imida,zolin-hydrochlorid als Ausgangs stoff verwendet. The 2 - [N - (4'-phenoxyphenyl) -N-benzyl-aminomethyl] -imidazoline thus obtained forms a hydrochloride in the form of colorless crystals which melt at 211 to 213. It should find pharmaceutical use or serve as an intermediate for the manufacture of medicinal products. SUBClaims: 1 .. Method according to claim, as characterized by the fact that a salt of a 2-halomethyl-imidazoline is used as the starting material. 2. The method according to claim, characterized in that 2 - chlorine methyl-imida, zoline hydrochloride is used as the starting material.
CH245895D 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline. CH245895A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242839T 1944-03-23
CH245895T 1944-03-23

Publications (1)

Publication Number Publication Date
CH245895A true CH245895A (en) 1946-11-30

Family

ID=25728743

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245895D CH245895A (en) 1944-03-23 1944-03-23 Process for the preparation of a new imidazoline.

Country Status (1)

Country Link
CH (1) CH245895A (en)

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