CH311677A - 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.

Info

Publication number
CH311677A
CH311677A CH311677DA CH311677A CH 311677 A CH311677 A CH 311677A CH 311677D A CH311677D A CH 311677DA CH 311677 A CH311677 A CH 311677A
Authority
CH
Switzerland
Prior art keywords
methyl
diethylamine
phenoxy
fatty acid
ethyl
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 CH311677A publication Critical patent/CH311677A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic 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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäureamides.   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäurea. mides, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich   abspaltenden    Rest bedeutet, mit   Diathylamin    umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten   reaktionsfähi-      en    Substituenten, wie z.   B.    einer Alkylsul  fonyloxy-oder Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den Diäthylaminrest erfolgt z. B. durch einfaehes Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin im   t'berschuss.    Das   N- [2- (4'-Methyl-phenoxy)-      äthyl-1]-N-methyl-diäthylaminoacetamid    ist ein farbloses, unter 0,04 mm bei 139-140  siedendes   Öl.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel :    22,    4 g   N- [2- (4-Methyl-phenoxy)-iith7l-l]-      N-methyl-ehloracetamid    und 22 g Diäthylamin werden zusammen in   150 em3    abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Re  aktionsgemisch wird    mit Wasser   ausgeschüt-    telt und dann mit 2n-Salzsäure ausgezogen.



  Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt md das   ausgesehiedene    Öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hoch  vacuum    destilliert.



   Dabei gewinnt man das unter 0,04 mm bei 139-140  siedende   N- [2- (4'-Methyl-phenoxy)-      äthyl-1]-N-methyl-diäthylaminoacetamid    als farbloses, säurelosliches   61.     



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäureamides,    dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2     
 in welcher X einen reaktionsfähigen, während der Reaktion sieh   abspaltenden    Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2-   (4'-Methyl-phenoxy)-äthyl-1]-      N-methyl-diäthylaminoacetamid    bildet ein farbloses, unter 0,04 mm bei 139-140  siedendes   01.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwischenprodukt Verwendung finden.



      UNTERANSPRUC   
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N- [2- (4'-Methyl   phenoxy)-äthyl-1]-N-methyl-halogenacetamid    mit Diäthylamin reagieren lässt. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  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 basic substituted fatty acid. mides, which is characterized in that a compound of the formula
EMI1.1
 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.



   The radical X can be in a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X against the diethylamine residue takes place z. B. by simple heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide is a colorless oil which boils at 139-140 below 0.04 mm.



   The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.



   Example: 22.4 g of N- [2- (4-methyl-phenoxy) -ith71-1] - N-methyl-chloroacetamide and 22 g of diethylamine are mixed together in 150 em3 abs. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid.



  The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide is added and the separated oil is absorbed in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide, boiling below 0.04 mm at 139-140, is obtained as colorless, acid-soluble 61.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
 in which X denotes a reactive radical which is split off during the reaction, with diethylamine. The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide obtained in this way forms a colorless oil, boiling below 0.04 mm at 139-140.



   The new amide will be used as a local anesthetic and as an intermediate product.



      UNDERCLAIMED
Process according to patent claim, characterized in that an N- [2- (4'-methyl phenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Process for the production of a new basic substituted fatty acid amide. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäurea. mides, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diathylamin umsetzt. The subject of the present patent is a process for the preparation of a new basic substituted fatty acid. mides, which is characterized in that a compound of the formula EMI1.1 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine. Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähi- en Substituenten, wie z. B. einer Alkylsul fonyloxy-oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Diäthylaminrest erfolgt z. B. durch einfaehes Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin im t'berschuss. Das N- [2- (4'-Methyl-phenoxy)- äthyl-1]-N-methyl-diäthylaminoacetamid ist ein farbloses, unter 0,04 mm bei 139-140 siedendes Öl. The radical X can be in a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X against the diethylamine residue takes place z. B. by simple heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide is a colorless oil which boils at 139-140 below 0.04 mm. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden. The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives. Beispiel : 22, 4 g N- [2- (4-Methyl-phenoxy)-iith7l-l]- N-methyl-ehloracetamid und 22 g Diäthylamin werden zusammen in 150 em3 abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Re aktionsgemisch wird mit Wasser ausgeschüt- telt und dann mit 2n-Salzsäure ausgezogen. Example: 22.4 g of N- [2- (4-methyl-phenoxy) -ith71-1] - N-methyl-chloroacetamide and 22 g of diethylamine are mixed together in 150 em3 abs. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted by shaking with water and then extracted with 2N hydrochloric acid. Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt md das ausgesehiedene Öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hoch vacuum destilliert. The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide is added and the separated oil is absorbed into ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum. Dabei gewinnt man das unter 0,04 mm bei 139-140 siedende N- [2- (4'-Methyl-phenoxy)- äthyl-1]-N-methyl-diäthylaminoacetamid als farbloses, säurelosliches 61. The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide, boiling below 0.04 mm at 139-140, is obtained as colorless, acid-soluble 61. PATENTANSPRUCH : Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI1.2 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2- (4'-Methyl-phenoxy)-äthyl-1]- N-methyl-diäthylaminoacetamid bildet ein farbloses, unter 0,04 mm bei 139-140 siedendes 01. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula EMI1.2 in which X denotes a reactive radical which is split off during the reaction, with diethylamine. The N- [2- (4'-methyl-phenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide obtained in this way forms a colorless oil, boiling below 0.04 mm at 139-140. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. The new amide will be used as a local anesthetic and as an intermediate product. UNTERANSPRUC Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N- [2- (4'-Methyl phenoxy)-äthyl-1]-N-methyl-halogenacetamid mit Diäthylamin reagieren lässt. UNDERCLAIMED Process according to patent claim, characterized in that an N- [2- (4'-methyl phenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine.
CH311677D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311677A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311677T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311677A true CH311677A (en) 1955-11-30

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ID=25735410

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311677D CH311677A (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) CH311677A (en)

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