CH240070A - Process for the preparation of a derivative of a carboxylic acid. - Google Patents

Process for the preparation of a derivative of a carboxylic acid.

Info

Publication number
CH240070A
CH240070A CH240070DA CH240070A CH 240070 A CH240070 A CH 240070A CH 240070D A CH240070D A CH 240070DA CH 240070 A CH240070 A CH 240070A
Authority
CH
Switzerland
Prior art keywords
soluble
derivative
carboxylic acid
preparation
acetic acid
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Cilag Chemisch Laboratorium
Original Assignee
Cilag Chemisches Ind Lab Ag
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 Cilag Chemisches Ind Lab Ag filed Critical Cilag Chemisches Ind Lab Ag
Publication of CH240070A publication Critical patent/CH240070A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids

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

  

  Verfahren zur Darstellung eines Abkömmlings einer     Karbonsäure.       Gegenstand der Erfindung ist ein Verfah  ren zur Gewinnung eines neuen Abkömmlings  einer     Karbonsäure    von der Formel  
EMI0001.0003     
    welcher gute     spasmolytische    Wirkung zeigt  und daher als Arzneimittel verwendet werden  soll.

   Das Verfahren ist dadurch gekennzeich  net, dass man     Morpholin    auf ein     Diphenyl-          halogen-essigsäurehalogenid    einwirken lässt,  wobei unter Abspaltung von     Halogenwasser-          stoff    das     Diphenyl    -     morpholino    -     essigsäure-          morpholid    entsteht.  



  <I>1.</I>     Ausführungsbeispiel:     Ein Gemisch von 10 g     Diphenyl    -     chlor-          essigsäurechlorid,    23 g     Morpholin    und 20 g  absolutem Alkohol wird 5 Stunden im Auto-    klauen auf etwa     150     C erhitzt. Das Reak  tionsprodukt wird, nach     Zufügen    von 10 g       Natriumbikarbonat,    im     Vakuum        zur    Trockne  eingedampft.

   Den Rückstand zieht man mit  Chloroform aus, wäscht die     Chloroformlösung     mit Wasser und     trocknet    sie über wasser  freiem     Natriumsulfat.    Beim Einengen der Lö  sung kristallisieren 12 g     Diphenyl-morpholino-          essigsäuremorpholid    aus.  



  <I>2.</I>     Ausführungsbeispiel     Zu einer     Lösung    von 2,8 g     Diphenyl-          brom    -     essigsäurebromid    in 5 cm' absolutem  Äther lässt man unter Rühren eine Lösung  von 3,5 g     Morpholin    in 10 cm' Äther zu  tropfen und kocht das Gemisch 4 Stunden am       Rückflusskühler.    Beim Aufarbeiten gemäss dem  Beispiel 1 wird das     Diphenyl    -     morpholino-          essigsäuremorpholid    in einer Ausbeute von  3,15 g erhalten.  



  Das Endprodukt des Verfahrens bildet  farblose, bei 148 bis 149  C schmelzende  Plättchen. Es ist leicht     löslich    in Chloroform,  mässig gut     löslich    in verdünnten Mineral-      Säuren, Benzol und Azeton, ziemlich schwer  löslich in Alkohol und schwerlöslich in Was  ser, Alkalien, Äther und     Petroläther.  



  Process for the preparation of a derivative of a carboxylic acid. The invention relates to a procedural Ren for obtaining a new derivative of a carboxylic acid of the formula
EMI0001.0003
    which shows good spasmolytic effect and should therefore be used as a medicine.

   The process is characterized in that morpholine is allowed to act on a diphenylhaloacetic acid halide, the diphenylmorpholinoacetic acid morpholide being formed with the elimination of hydrogen halide.



  <I> 1. </I> Exemplary embodiment: A mixture of 10 g of diphenyl chloroacetic acid chloride, 23 g of morpholine and 20 g of absolute alcohol is heated to around 150 ° C. for 5 hours in a car. The reaction product is, after adding 10 g of sodium bicarbonate, evaporated to dryness in vacuo.

   The residue is extracted with chloroform, the chloroform solution is washed with water and dried over anhydrous sodium sulfate. When the solution is concentrated, 12 g of diphenylmorpholino-acetic acid morpholide crystallize out.



  <I> 2nd </I> exemplary embodiment A solution of 3.5 g of morpholine in 10 cm of ether is allowed to drip into a solution of 2.8 g of diphenyl bromoacetic acid bromide in 5 cm of absolute ether and is boiled the mixture for 4 hours on the reflux condenser. When working up according to Example 1, the diphenylmorpholino-acetic acid morpholide is obtained in a yield of 3.15 g.



  The end product of the process is colorless platelets that melt at 148 to 149 ° C. It is easily soluble in chloroform, moderately soluble in dilute mineral acids, benzene and acetone, fairly sparingly soluble in alcohol and sparingly soluble in water, alkalis, ether and petroleum ether.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Abkömm lings einer Karbonsäure, dadurch gekenn zeichnet, dass man 141orpholin auf ein Diplieny 1- halogen - essigsäurehalogenid einwirken lälät, wobei unter Abspaltung von Halogenwasser- stoff Diphenyl-morpholino-essigsäureniorpliolid entsteht. PATENT CLAIM: Process for the preparation of a derivative of a carboxylic acid, characterized in that 141 morpholine is allowed to act on a Diplieny 1-haloacetic acid halide, whereby diphenyl-morpholino-acetic acid orpliolide is formed with elimination of hydrogen halide. Der Endstoff stellt farblose Plättchen vom Schmelzpunkt 148 bis 149 C dar, ist leicht löslich in Chloroform, mässig gut löslich in verdünnten i@linera.lsäuren, Benzol und Aze- ton, ziemlich schwer löslich in Alkohol und sches ei-lüslich in Wasser, Alkalien, Äther und Petrolätlier. Er soll therapeutisch verwendet werden. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man Diplienyl-clilor-essig- säurechlorid verwendet. 2. The end product is colorless platelets with a melting point of 148 to 149 C, is easily soluble in chloroform, moderately soluble in dilute linear acids, benzene and acetone, fairly sparingly soluble in alcohol and quite soluble in water and alkalis , Ether and petroleum etlier. It is intended to be used therapeutically. SUBClaims: 1. Method according to claim, characterized in that diplienyl-clilor-acetic acid chloride is used. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, da1:> nia.n das 1Vlorpholin und das Diphenyl- chlor-essigsii.ureclilorid auf etwa 150 C er hitzt. Process according to patent claim and dependent claim 1, characterized in that:> nia.n the 1Vlorpholine and the diphenylchloro-acetic ureclloride are heated to about 150 C.
CH240070D 1944-07-29 1944-07-29 Process for the preparation of a derivative of a carboxylic acid. CH240070A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH240070T 1944-07-29

Publications (1)

Publication Number Publication Date
CH240070A true CH240070A (en) 1945-11-30

Family

ID=4461604

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240070D CH240070A (en) 1944-07-29 1944-07-29 Process for the preparation of a derivative of a carboxylic acid.

Country Status (1)

Country Link
CH (1) CH240070A (en)

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