CH311576A - Process for the production of a new basic substituted fatty acid amide. - Google Patents

Process for the production of a new basic substituted fatty acid amide.

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Publication number
CH311576A
CH311576A CH311576DA CH311576A CH 311576 A CH311576 A CH 311576A CH 311576D A CH311576D A CH 311576DA CH 311576 A CH311576 A CH 311576A
Authority
CH
Switzerland
Prior art keywords
fatty acid
substituted fatty
production
ethyl
acid amide
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag 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 Ag filed Critical Cilag Ag
Publication of CH311576A publication Critical patent/CH311576A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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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 basisch substituierten   Fettsäureamides.   



   Gegenstand des   vorliegenden Patentes    ist   cin    Verfahren zur Herstellung eines neuen   basisel substituierten Fettsaureamides,    wel  ehes dadurch gekennzeiehnet    ist, dass man auf eine Verbindung der Formel
EMI1.1     
 eine Verbindung der Formel
EMI1.2     
 in welchen Formeln   X    und y reaktionsfähige,   hei der    Reaktion sich abspaltende Reste bedeuten, einwirken lässt.



   Als Verbindungen der Formel   I kommen    für einen Umsatz beispielsweise in Frage : Das freie Amin (Y = H), aber   aueh dessen      salé,    wie beispielsweise das   Hydroeblorid    oder das Sulfat.



   Als Verwindungen der Formel II kommen beispielsweise in Frage :   Diäthylaminoessig-      saure    selbst   und ihre reaktionsfähigen    funktionellen Derivate wie ihre   Halogenide, ihre    Ester, ihre Anhydride, beispielsweise die reinen und nach die gemischten Anhydride mit Phosphorsäure, Schwefelsäure und Kohlensäure usf.



   MAn kann beispielsweise   N-[o-(3'-Methoxy-    phenoxy)-äthyl-1]-N-methylamin oder auch ein Salz desselben in Gegenwart eines   fur    diese Zweeke geeigneten wasserabspaltenden   3Iittels wie Phosphorpentoxyd, Phosphoroxy-    chlorid use, mit Diäthylaminoessigsäure behandeln.



   Weiter kann man auch N- [2- (3'-Methoxyphenoxy)-äthyl-1]-N-methyl;amin bzw. ein Salz desselben mit einem   Diäthylaminoessigsäure-    halogenid (bzw. einem Salz eines solchen) oder einem Anhydrid zur Reaktion bringen.



   Es   ist weiterhin auch moglich, N- [2- (3 =    MEthoxy-phenoxy)-äthyl-1]-N-methylamin mit einem :   Didthylaminoessigsaureester,    vorzugsweise einem Arylester, bei erhöhter Tempera  tur    zu acylieren.



   Das   au dise    Weise   erhaltene N-[2-(3'-       Methoxy-phenoxy)-äthyl-1]-N-methyl-diäthyl-    amino-acetamid bildet ein farbloses, unter 0, 06 mm bei 157-158  siedendes   61.   



   Das neue Amid soll als Lokalanästhetikum und als Zwisechenprodukt zur   Eerstellung wei-      terer    Derivate   Verwendlmg finden.   



   Beispiel :
17 g N-[2-(3'-Methoxy-phenoxy)-äthyl-1] N-methylamin in Benzol werden mit einer Mischung von 18   g Diäthylaminoessigsäure-      ehlorid-hydrochlorid lmd    20 g Triäthylamin erwärm. Anschliessend wird das   geXildete    Triäthylaminhydrochlorid durch Ausschütteln mit   Wasser entfernt,    die   Benzoll6sung    nach dem Trocknen verdampft und der   Rüek-    stand im hochvakuum destilliert. Man erhält so in guter Ausbeute das N- [2- (3'-Methoxyphenoxy)-äthyl-1]-N-methyl-diäthylamino   acetamid, welehes    ein unter 0, 06 mm bei 157 bis   158     siedendes farbloses   01    darstellt.



     Die CReaktion kann aueh    ohne   Verdün-    nungs-und Kondensationsmittel durchgeführt werden, indem man beispielsweise dasn N-[2 (3'-Methoxy-Phenoxy)-äthyl-1]-N-methylamin mit Diäthylaminoessigsäure-chlorid-hydrochlorid   troeken    erhitzt,   anschliel3end die Reak-      tionsmasse    mit Wasser verdünnt und in   oubli-    cher   Weise auíarbeitet.  



  



  Process for the production of a new basic substituted fatty acid amide.



   The subject of the present patent is a process for the preparation of a new base-substituted fatty acid amide, which is marked by the fact that a compound of the formula
EMI1.1
 a compound of the formula
EMI1.2
 in which formulas X and y mean reactive radicals which are split off during the reaction, can act.



   Compounds of the formula I that can be used for a conversion are, for example: The free amine (Y = H), but also its salé, such as, for example, the hydrochloride or the sulfate.



   Twists of the formula II include, for example: diethylaminoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and mixed anhydrides with phosphoric acid, sulfuric acid and carbonic acid etc.



   For example, N- [o- (3'-methoxyphenoxy) ethyl-1] -N-methylamine or a salt thereof can be treated with diethylaminoacetic acid in the presence of a dehydrating agent suitable for these purposes, such as phosphorus pentoxide or phosphorus oxychloride .



   N- [2- (3'-methoxyphenoxy) ethyl-1] -N-methyl; amine or a salt thereof can also be reacted with a diethylaminoacetic acid halide (or a salt of such) or an anhydride .



   It is also possible to acylate N- [2- (3 = methoxy-phenoxy) -ethyl-1] -N-methylamine with a didthylaminoacetic acid ester, preferably an aryl ester, at elevated temperature.



   The N- [2- (3'-methoxyphenoxy) -ethyl-1] -N-methyl-diethylamino-acetamide obtained in this way forms a colorless 61 boiling below 0.06 mm at 157-158.



   The new amide is to be used as a local anesthetic and as an intermediate product for the preparation of further derivatives.



   Example:
17 g of N- [2- (3'-methoxyphenoxy) ethyl-1] N-methylamine in benzene are heated with a mixture of 18 g of diethylaminoacetic acid chloride hydrochloride and 20 g of triethylamine. The triethylamine hydrochloride formed is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum. The N- [2- (3'-methoxyphenoxy) ethyl-1] -N-methyl-diethylamino acetamide, which is a colorless oil boiling below 0.06 mm at 157 to 158, is thus obtained in good yield.



     The C reaction can also be carried out without a diluent and condensing agent, for example by heating the N- [2 (3'-methoxy-phenoxy) -ethyl-1] -N-methylamine to dryness with diethylaminoacetic acid chloride hydrochloride, then heating the Reaction mass diluted with water and worked up in an obvious way.

 

Claims (1)

PATENTANSPRUCHE: Verfahren zur Herstellung eines nenen basisch substituierten Fettsäreamides, dadurch gekennzeichnet, dass man auf eine Verbindung der formel EMI2.1 eine Verbindung der Formel EMI2.2 in welchen If ormeln X und Y reaktionsfähige, bei der Reaktion sieh abspaltende Reste bedeuten, einwirken lässt. PATENT CLAIMS: Process for the preparation of a basic substituted fatty acid mixture, characterized in that a compound of the formula EMI2.1 a compound of the formula EMI2.2 in which If-formulas X and Y mean reactive residues that split off during the reaction, can act. Das auf diese Wesie erhaltene N-'2-(3' Methoxy-phenoxy)-äthyl-1]-N-methyl-diäthyla. mino-acetamid ist ein farbloses, unter 0, 06 mm bei 157158 siedendes (il. The N-'2- (3 'methoxyphenoxy) -ethyl-1] -N-methyl-diethyla obtained in this way. mino-acetamide is a colorless, boiling below 0.06 mm at 157158 (il. Das neue Ainid soll als Loliala. nasthetikum nnd als Zwischenprodukt. Verwendung finden. The new ainid is said to be Loliala. Aesthetic and as an intermediate. Find use. UNTERANSPRUCH: Verfahren naeh Patentanspruch, dadurch gekennzcichnet, dass man N-[2-(3'-Methoxyphenoxy)-äthyl-1]-N-methylamin mit einem Diäthylaminoessigsäurehalogenid umsetzt. SUBCLAIM: Method according to patent claim, characterized in that N- [2- (3'-methoxyphenoxy) ethyl-1] -N-methylamine is reacted with a diethylaminoacetic acid halide.
CH311576D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311576A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311576T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311576A true CH311576A (en) 1955-11-30

Family

ID=25735103

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311576D CH311576A (en) 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide.

Country Status (1)

Country Link
CH (1) CH311576A (en)

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