CH311681A - 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
CH311681A
CH311681A CH311681DA CH311681A CH 311681 A CH311681 A CH 311681A CH 311681D A CH311681D A CH 311681DA CH 311681 A CH311681 A CH 311681A
Authority
CH
Switzerland
Prior art keywords
diethylamine
phenoxy
ethyl
oxy
methyl
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 CH311681A publication Critical patent/CH311681A/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

Landscapes

  • 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 FettsÏureamides.



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten FettsÏureamides, wel  elles      dadureh    gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
   m weicher X einen reaktionsfähigen, während      der Reaktion sieh    abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem. sonstigen für den Austausch gegen den basisehen Rest geeigneten reaktionsfähig Substituenten, wie z. B. einer Alkylsulfonyloxy- oder   Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den   Diäthylaminrest    erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden   Konden-    sationsmittels, oder von   Diäthvlamin    im ¯ber   sehuss Das N-[2-(4'-Oxv-phenoxy)-äthyl-1]-    N-methyl-diÏthylamino-acetamid bildet farblose,   bei 63-65  schmelzende Kristalle.   



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



   Beispiel :  ''2,   7    g N- [2-   (4'-Oxy-phenoxy)-äthyl-1]-N-    methyl-chloracetamid und 19 g DiÏthylamin werden zusammen in 150 cm3 abs. Benzol 5 Stunden auf dem Wasserbad erhitzt. Das   Re-    aktionsgemiseh wird mit Wasser   ausgeschüt-    telt und dann mit 2n-Salzsäure ausgezogen.



  Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Na  tronlauge    versetzt und das ausgeschiedene   61    in Äther aufgenommen. Nach dem Trocknen   der Ätherauszüge über Pottasche    wird der Äther verdampft und der   Riiekstand    im Hochvakuum destilliert.



   Dabei gewinnt man das bei 63-65    schmel-    zende N- [2- (4'-Oxy-phenoxy)-äthyl-1]-N-me  thyl-diäthylamino-acetamid.     



   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 sich abspaltenden Rest bedeutet. mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2- (4'-Oxy-phenoxy)-äthyl-1]-Nmethyl-diäthylamino-acetamid bildet farblose, bei 63-65  schmelzende Kristalle.



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



   UNTERANSPRUCH :
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N- [2- (4'-Oxy   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 forms a process for the preparation of a new basic substituted FettsÏureamides, wel elles is characterized by the fact that a compound of the formula
EMI1.1
   m softer X means a reactive radical which is split off during the reaction and reacts with diethylamine.



   The radical X can be in a halogen atom or a. other reactive substituents suitable for replacement against the basic group, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the diethylamine residue takes place z. B. by simply heating with diethylamine, if necessary in the presence of a basic condensing agent, or diethvlamine in excess of the N- [2- (4'-Oxv-phenoxy) -ethyl-1] -N-methyl-diethylamino Acetamide forms colorless crystals that melt at 63-65.



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



   Example: '' 2.7 g of N- [2- (4'-oxy-phenoxy) -ethyl-1] -N-methyl-chloroacetamide and 19 g of diethylamine are combined in 150 cm3 of abs. Benzene heated on a water bath for 5 hours. The reaction mixture is shaken out with water and then extracted with 2N hydrochloric acid.



  The hydrochloric acid extract is then extracted with ether, with conc. Added sodium hydroxide solution and the excreted 61 was taken up 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'-oxy-phenoxy) -ethyl-1] -N-methyl-diethylamino-acetamide which melts at 63-65 is obtained.



   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 is a reactive radical which is split off during the reaction. Reacts with diethylamine. The N- [2- (4'-oxy-phenoxy) -ethyl-1] -Nmethyl-diethylamino-acetamide obtained in this way forms colorless crystals which melt at 63-65.



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



   SUBClaim:
Process according to patent claim, characterized in that an N- [2- (4'-oxy 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 FettsÏureamides. 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 FettsÏureamides, wel elles dadureh gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 m weicher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. The subject of the present patent forms a process for the preparation of a new basic substituted FettsÏureamides, wel elles is characterized by the fact that a compound of the formula EMI1.1 m softer X means a reactive radical which is split off during the reaction and reacts with diethylamine. Der Rest X kann in einem Halogenatom oder einem. sonstigen für den Austausch gegen den basisehen Rest geeigneten reaktionsfähig Substituenten, wie z. B. einer Alkylsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Diäthylaminrest erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Konden- sationsmittels, oder von Diäthvlamin im ¯ber sehuss Das N-[2-(4'-Oxv-phenoxy)-äthyl-1]- N-methyl-diÏthylamino-acetamid bildet farblose, bei 63-65 schmelzende Kristalle. The radical X can be in a halogen atom or a. other reactive substituents suitable for replacement against the basic group, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the diethylamine residue takes place z. B. by simply heating with diethylamine, if necessary in the presence of a basic condensing agent, or diethvlamine in excess of the N- [2- (4'-Oxv-phenoxy) -ethyl-1] -N-methyl-diethylamino Acetamide forms colorless crystals that melt at 63-65. 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 : ''2, 7 g N- [2- (4'-Oxy-phenoxy)-äthyl-1]-N- methyl-chloracetamid und 19 g DiÏthylamin werden zusammen in 150 cm3 abs. Benzol 5 Stunden auf dem Wasserbad erhitzt. Das Re- aktionsgemiseh wird mit Wasser ausgeschüt- telt und dann mit 2n-Salzsäure ausgezogen. Example: '' 2.7 g of N- [2- (4'-oxy-phenoxy) -ethyl-1] -N-methyl-chloroacetamide and 19 g of diethylamine are combined in 150 cm3 of abs. Benzene heated on a water bath for 5 hours. The reaction mixture is shaken out with water and then extracted with 2N hydrochloric acid. Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Na tronlauge versetzt und das ausgeschiedene 61 in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Riiekstand im Hochvakuum destilliert. The hydrochloric acid extract is then extracted with ether, with conc. Added sodium hydroxide solution and the excreted 61 was taken up in 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 bei 63-65 schmel- zende N- [2- (4'-Oxy-phenoxy)-äthyl-1]-N-me thyl-diäthylamino-acetamid. The N- [2- (4'-oxy-phenoxy) -ethyl-1] -N-methyl-diethylamino-acetamide which melts at 63-65 is obtained. 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 sich abspaltenden Rest bedeutet. mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2- (4'-Oxy-phenoxy)-äthyl-1]-Nmethyl-diäthylamino-acetamid bildet farblose, bei 63-65 schmelzende Kristalle. 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 is a reactive radical which is split off during the reaction. Reacts with diethylamine. The N- [2- (4'-oxy-phenoxy) -ethyl-1] -Nmethyl-diethylamino-acetamide obtained in this way forms colorless crystals which melt at 63-65. 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. UNTERANSPRUCH : Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N- [2- (4'-Oxy phenoxy)-äthyl-1]-N-methyl-halogenacetamid mit Diäthylamin reagieren lässt SUBClaim: Process according to patent claim, characterized in that an N- [2- (4'-oxy phenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine
CH311681D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311681A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311681T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311681A true CH311681A (en) 1955-11-30

Family

ID=25735414

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311681D CH311681A (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) CH311681A (en)

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