CH139414A - Process for the preparation of a one-sided heterocyclically acylated diamine. - Google Patents

Process for the preparation of a one-sided heterocyclically acylated diamine.

Info

Publication number
CH139414A
CH139414A CH139414DA CH139414A CH 139414 A CH139414 A CH 139414A CH 139414D A CH139414D A CH 139414DA CH 139414 A CH139414 A CH 139414A
Authority
CH
Switzerland
Prior art keywords
preparation
sided
heterocyclically
acid
acylated diamine
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH139414A publication Critical patent/CH139414A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines einseitig     heteroeykliseh        aeylierten        Diamins.       Es wurde gefunden, dass man zu einem  einseitig     heterocyklisch        acylierten        Diamin    ge  langen kann, wenn man asymmetrisches     Di-          äthyläthylendiamin    mit einer Verbindung von  der Formel  
EMI0001.0009     
    in welcher R einen bei der Reaktion sich  abspaltenden Rest bedeutet, wie zum Beispiel  die     9-Acridincarbonsäure,    ihr     Anhydrid,    ihre  Ester oder ihre     Säurehalogenide,

      in letzterem  Falle zweckmässig unter Verwendung säure  bindender Mittel, zur Reaktion bringt.  



  Das     9-Acridincarbonsäure-diäthyiäthylen-          diamid    bildet schwach gelbe Blättchen vom       Smp.        105-1060,    die in Äther und Alkohol  leicht, in kaltem Benzol sowie in     Petroläther       schwer löslich sind. Die Salze der Base sind  in Wasser leicht löslich.  



  Die neue Verbindung soll zu therapeutischen  Zwecken Verwendung finden.  



       Beispiel:     1 Teil     9-Acridinoarbonsäure    wird durch  Behandlung mit 1,1 Teilen     Phosphorpenta-          chlorid    in ihr Chlorid verwandelt. Letzteres  wird nach Entfernung des     Phosphoroxychlorides     im Vakuum mit einer Lösung von 1,5 Teilen  asymmetrischem     Diäthyläthylendiamin    in To  luol versetzt. Nach beendigter Reaktion zieht  man die neue Base mit verdünnter Säure aus,  versetzt mit Soda und nimmt sie in Äther  auf. Nach Vertreibung des Lösungsmittels  wird das     9-AcridincarbonsäLire-diäthyläthyl-          endiamid    durch Kristallisation aus Benzol  gereinigt.  



  An Stelle von überschüssiger Base können  auch andere säurebindende Mittel, zum Beispiel       Alkalihydroxyde    oder     -karbonate,    Verwendung       finden.  



  Process for the preparation of a unilaterally heteroeyclic aylated diamine. It has been found that you can ge to a unilaterally heterocyclic acylated diamine if you use asymmetric diethylethylenediamine with a compound of the formula
EMI0001.0009
    in which R denotes a radical which is split off during the reaction, such as 9-acridinecarboxylic acid, its anhydride, its ester or its acid halide,

      in the latter case expediently using acid-binding agents to react.



  The 9-acridinecarboxylic acid diethyiethylenediamide forms pale yellow leaflets with a melting point of 105-1060, which are easily soluble in ether and alcohol, but poorly soluble in cold benzene and petroleum ether. The salts of the base are easily soluble in water.



  The new compound is intended to be used for therapeutic purposes.



       Example: 1 part of 9-acridinoarboxylic acid is converted into its chloride by treatment with 1.1 parts of phosphorus pentachloride. After removing the phosphorus oxychloride in vacuo, the latter is treated with a solution of 1.5 parts of asymmetrical diethylethylenediamine in toluene. When the reaction is complete, the new base is extracted with dilute acid, soda is added and it is taken up in ether. After driving off the solvent, the 9-acridincarboxylic acid diethylethylenediamide is purified by crystallization from benzene.



  Instead of excess base, other acid-binding agents, for example alkali hydroxides or carbonates, can also be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines einseitig heterocyklisch acylierten Diamins, dadurch gekennzeichnet, dass man asymmetrisches Di- äthyläthylendiamin mit einer Verbindung von der Formel EMI0002.0007 in welcher R einen bei der Reaktion sich ab spaltenden Rest bedeutet, zur Reaktion bringt. PATENT CLAIM: Process for the preparation of a one-sided heterocyclic acylated diamine, characterized in that asymmetric diethylethylenediamine with a compound of the formula EMI0002.0007 in which R is a radical which splits off during the reaction, brings about the reaction. Das 9-Acridincarbonsäure-diäthyläthylen- diamid bildet schwach gelbe Blättchen vom Smp. 10"0-106 , die in Äther und Alkohol leicht, in kaltem Benzol sowie in Petroläther schwer löslich sind. Die Salze der Base sind in Wasser leicht löslich. Die neue Verbindung soll zu therapeutischen Zwecken Verwendung finden. The 9-acridinecarboxylic acid diethylethylene diamide forms pale yellow leaflets with a m.p. Compound is intended to be used for therapeutic purposes.
CH139414D 1927-11-19 1927-11-19 Process for the preparation of a one-sided heterocyclically acylated diamine. CH139414A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139414T 1927-11-19
CH137337T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139414A true CH139414A (en) 1930-04-15

Family

ID=25712915

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139414D CH139414A (en) 1927-11-19 1927-11-19 Process for the preparation of a one-sided heterocyclically acylated diamine.

Country Status (1)

Country Link
CH (1) CH139414A (en)

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