CH311675A - 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
CH311675A
CH311675A CH311675DA CH311675A CH 311675 A CH311675 A CH 311675A CH 311675D A CH311675D A CH 311675DA CH 311675 A CH311675 A CH 311675A
Authority
CH
Switzerland
Prior art keywords
butylamine
methyl
ethyl
radical
fatty acid
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 CH311675A publication Critical patent/CH311675A/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
    • C07D295/04Heterocyclic 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
    • C07D295/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02Carboxylic 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
    • 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 bildet ein Verfahren zur Herstellung   eilleS    neuen basisch substituierten Fettsäureamides, welches dadurch gekennzcichnet ist,   dal3 man    eine Verbindung der Formel
EMI1.1     
 in weleher X einen reaktionsfähgien, während der Reaktion sich abspaltenden Rest bedeutet, mit n-Butylamin umsetzt.



   D er Rest   A : kann    in einem halogenatom oder einem sonstigen für den Austausch genen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer alkylsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen. I) er Austausch der Gruppe X gegen den n-Butylaminrest erfolgt z. B. durch einfaehes Erwärmen mit n-Butylamin gegebenenfalls in Gegenart eines basisch reagierenden Konden  aationsmittels oder    von n-Butylamin im   ITber-    sehuss. Das N-[2-Methyl-phenoxy)-äethyl-1] N-methyl-N'-n-butylamino-acetamid ist ein farbolses, unter 0, 25 mm bei 181-183  siedendes Öl.



     I) as neue Amid    soll als Lokalanästhetikum und als Zwischenprodukt zur herstellung weiterer Derivate Verwendung finden.



     Be. ispiel    :
24 g N-[2-(2'-Methyl-phenopxy)-ätjyl-1]-Nmethyl-chloracetamid und 14,6 g n-Butylamin werden zusammen in 150 cm3 bas. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Reaktionsgemisch wird mit Wasser ausgeschüttelt und dann   mit  n-Salzsäure ausgezogen.   



  Darauf wird   der    salzaure   Auszug    mit Ather extrahiert, unter Eiskühlung mit konz. Natronglauge versetzt und das ausgeschiedene   () I      in-Xther aufgenomnien. Nach    dem Troclinen der Ätherauszüge über Pottasche wird der Äther versampft und der Rückstand im Hochvakuum destilliert.



   Dabei   gewimlt man Åaas unter    0, 25 mm bei   181183     siedende   N-[2-(2'-Alethyl-phenoxy)-    äthyl-1]-N-methyl-N'-n-butylaminoacetamid in einer   Ausbeute    von   50 /o    der Theorie. Farbloses   Ol, schwer loslich    in Wasser, gut in organischen Lösungsmittlen und in verdünnten Minerlasäuren.  



     PATENTANSPRLTCH    :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbin  dung    der Formel.
EMI1.2     
 in weleher X einen reaktionsfäghigen, während der   Reaktioll sich    abspaltenden Rest bedeutet, mit n-Butylamin umsetzt. Das   auf diese    Weise erhaltene N-[2-(2'-Methyl-phenoxy)-äthyl-1] 

**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 all new basic substituted fatty acid amides, 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 and reacts with n-butylamine.



   D he radical A: can be present in a halogen atom or another reactive substituent suitable for the exchange of the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. I) he exchange of the group X against the n-butylamine radical takes place z. B. by simple heating with n-butylamine, optionally in the presence of a basic condensation agent or n-butylamine in excess of IT. N- [2-methyl-phenoxy) -ethyl-1] N-methyl-N'-n-butylamino-acetamide is a color-oily oil that boils below 0.25 mm at 181-183.



     I) the new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.



     Be. ispiel:
24 g of N- [2- (2'-methyl-phenopxy) -ethyl-1] -Nmethyl-chloroacetamide and 14.6 g of n-butylamine are combined in 150 cm3 bas. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted with water and then extracted with n-hydrochloric acid.



  Then the salt-acid extract is extracted with ether, with ice-cooling with conc. Sodium liquor was added and the excreted () I was taken up in-Xther. After troclining the ether extracts over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   In doing so, N- [2- (2'-alethyl-phenoxy) -ethyl-1] -N-methyl-N'-n-butylaminoacetamide boiling below 0.25 mm at 181183 is obtained in a yield of 50% of theory . Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids.



     PATENT APPLICATION:
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, while the Reaktioll means splitting off radical, reacts with n-butylamine. The N- [2- (2'-methyl-phenoxy) -ethyl-1] obtained in this way

** 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 eilleS neuen basisch substituierten Fettsäureamides, welches dadurch gekennzcichnet ist, dal3 man eine Verbindung der Formel EMI1.1 in weleher X einen reaktionsfähgien, während der Reaktion sich abspaltenden Rest bedeutet, mit n-Butylamin umsetzt. The subject of the present patent is a process for the preparation of all new basic substituted fatty acid amides, 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 and reacts with n-butylamine. D er Rest A : kann in einem halogenatom oder einem sonstigen für den Austausch genen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer alkylsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen. I) er Austausch der Gruppe X gegen den n-Butylaminrest erfolgt z. B. durch einfaehes Erwärmen mit n-Butylamin gegebenenfalls in Gegenart eines basisch reagierenden Konden aationsmittels oder von n-Butylamin im ITber- sehuss. Das N-[2-Methyl-phenoxy)-äethyl-1] N-methyl-N'-n-butylamino-acetamid ist ein farbolses, unter 0, 25 mm bei 181-183 siedendes Öl. D he radical A: can be present in a halogen atom or another reactive substituent suitable for the exchange of the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. I) he exchange of the group X against the n-butylamine radical takes place z. B. by simple heating with n-butylamine, optionally in the presence of a basic condensation agent or n-butylamine in excess of IT. N- [2-methyl-phenoxy) -ethyl-1] N-methyl-N'-n-butylamino-acetamide is a color-oily oil that boils below 0.25 mm at 181-183. I) as neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur herstellung weiterer Derivate Verwendung finden. I) the new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. Be. ispiel : 24 g N-[2-(2'-Methyl-phenopxy)-ätjyl-1]-Nmethyl-chloracetamid und 14,6 g n-Butylamin werden zusammen in 150 cm3 bas. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Reaktionsgemisch wird mit Wasser ausgeschüttelt und dann mit n-Salzsäure ausgezogen. Be. ispiel: 24 g of N- [2- (2'-methyl-phenopxy) -ethyl-1] -Nmethyl-chloroacetamide and 14.6 g of n-butylamine are combined in 150 cm3 bas. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted with water and then extracted with n-hydrochloric acid. Darauf wird der salzaure Auszug mit Ather extrahiert, unter Eiskühlung mit konz. Natronglauge versetzt und das ausgeschiedene () I in-Xther aufgenomnien. Nach dem Troclinen der Ätherauszüge über Pottasche wird der Äther versampft und der Rückstand im Hochvakuum destilliert. Then the salt-acid extract is extracted with ether, with ice-cooling with conc. Sodium liquor was added and the excreted () I was taken up in-Xther. After troclining the ether extracts over potash, the ether is evaporated and the residue is distilled in a high vacuum. Dabei gewimlt man Åaas unter 0, 25 mm bei 181183 siedende N-[2-(2'-Alethyl-phenoxy)- äthyl-1]-N-methyl-N'-n-butylaminoacetamid in einer Ausbeute von 50 /o der Theorie. Farbloses Ol, schwer loslich in Wasser, gut in organischen Lösungsmittlen und in verdünnten Minerlasäuren. In doing so, N- [2- (2'-alethyl-phenoxy) -ethyl-1] -N-methyl-N'-n-butylaminoacetamide boiling below 0.25 mm at 181183 is obtained in a yield of 50% of theory . Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids. PATENTANSPRLTCH : Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbin dung der Formel. EMI1.2 in weleher X einen reaktionsfäghigen, während der Reaktioll sich abspaltenden Rest bedeutet, mit n-Butylamin umsetzt. Das auf diese Weise erhaltene N-[2-(2'-Methyl-phenoxy)-äthyl-1] N-methyl-N'-n-butylamino-acetamid bildet ein farbloses, unter 0, 25 mm bei 181-183 siedendes 61. PATENT APPLICATION: 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, while the Reaktioll means splitting off radical, reacts with n-butylamine. The N- [2- (2'-methyl-phenoxy) -ethyl-1] N-methyl-N'-n-butylamino-acetamide obtained in this way forms a colorless 61, boiling below 0.25 mm at 181-183 . Das neue Amid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. The new amide is to be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH : Verfahren nach Patentansprncl, dadureh gekennzeichnet, dass man ein N-[2-(2'-Methyl phenoxy)-äthyl-l]-N-methvl-halogen-aeetamid mit n-Butylamin reagieren lässt. SUBClaim: Process according to patent claim, characterized in that an N- [2- (2'-methyl phenoxy) ethyl-1] -N-methvl-halogeno-ethamide is allowed to react with n-butylamine.
CH311675D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311675A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311675T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311675A true CH311675A (en) 1955-11-30

Family

ID=25735408

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311675D CH311675A (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) CH311675A (en)

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