CH311686A - 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
CH311686A
CH311686A CH311686DA CH311686A CH 311686 A CH311686 A CH 311686A CH 311686D A CH311686D A CH 311686DA CH 311686 A CH311686 A CH 311686A
Authority
CH
Switzerland
Prior art keywords
production
fatty acid
substituted fatty
acid amide
new basic
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 CH311686A publication Critical patent/CH311686A/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
    • C07D295/145—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  verfahren zur Herstellung eines neuen basisch substituierten     Fettsäureamides.            Gegenstand    des vorliegenden Patentes bil  det ein Verfahren zur Herstellung eines neuen  basisch substituierten     Fettsäureamides,    wel  ehes dadurch gekennzeichnet ist, dass man eine  Verbindung der Formel  
EMI0001.0004     
    in welcher X einen reaktionsfähigen, während  der Reaktion sich abspaltenden Rest bedeutet,  mit     2-Methyl-piperidin    umsetzt.  



  Der Rest. X kann in einem     IIalogenatoin     oder einem sonstigen für den Austausch gegen  den basischen Rest geeigneten     reaktionsfähi-          ;ren        Substituenten,    wie z. B. einer     Alkjsul-          fonyloxy-    oder     Arylsulfonyloxygruppe,    beste  hen. Der     Austausch    der Gruppe X gegen den       2-Methyl-piperidinorest    erfolgt z.

   B. durch ein  faelies Erwärmen mit     2-Methyl-piperidin,    ge  gebenenfalls in     Gegenwart    eines basisch reagie  renden     Kondensationsmittels    oder von     2-Me-          thyl-piperidin    im     übersehuss.    Das     a-Methyl-          piperidino-essigsäure-N-        [3-(2',4',6'-trimethyl-          pbenoxy)-propyl-2]-metliylamid    ist ein farb  loses, unter<B>0,01</B>     inm    bei 179-180  siedendes  Öl.  



  Das neue     Amid    soll als     Lokalanästhetikiun     und als Zwischenprodukt zur Herstellung wei  terer Derivate     Verwendung    finden.    <I>Beispiel:</I>  38,3 g     Chloressigsäiire-N-[3-(2',4',6'-trime-          thyl-phenoxy)-propyl-2]-methylamid    und 19,8 g  2 -     hlethyl    -     piperidin    werden zusammen in  200     em3        abs.    Benzol 3 Stunden auf dem Was  serbad erhitzt. Das Reaktionsgemisch wird mit  Wasser ausgeschüttelt und dann mit     2n-Salz-          säure    ausgezogen.

   Darauf wird der     salzsaure     Auszug mit Äther extrahiert, unter Eisküh  lung mit     konz.    Natronlauge versetzt und das  ausgeschiedene Öl in Äther aufgenommen.  Nach dem Trocknen der Ätherauszüge über  Pottasche wird der Äther verdampft und der  Rückstand im Hochvakuum destilliert.  



  Dabei gewinnt man das unter 0,01 mm bei  179-180  siedende     a-Methyl-piperidino-essig-          säure-N-    [     3-(2',4',6'-trimethyl-phenoxy)        -propyl-          2]        -methylamid    in einer Ausbeute von     65'II/a    der  Theorie. Farbloses Öl, schwer löslich in Was  ser, gut in organischen Lösungsmitteln und in  verdünnten Mineralsäuren.



  process for the production of a new basic substituted fatty acid amide. The subject of the present patent bil det a process for the preparation of a new basic substituted fatty acid amide, wel ehes is characterized in that a compound of the formula
EMI0001.0004
    in which X is a reactive radical which is split off during the reaction, is reacted with 2-methylpiperidine.



  The radical. X can be in an analogue or other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkysulfonyloxy or arylsulfonyloxy group exist. The exchange of the group X against the 2-methyl-piperidino radical takes place, for.

   B. by incorrect heating with 2-methyl-piperidine, if necessary in the presence of a basic reacting condensing agent or 2-methyl-piperidine in excess. The a-methylpiperidino-acetic acid-N- [3- (2 ', 4', 6'-trimethyl-pbenoxy) -propyl-2] -metliylamide is a colorless, below <B> 0.01 </ B > in oil boiling at 179-180.



  The new amide is intended to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 38.3 g of chloroacetic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide and 19.8 g of 2 - Hlethyl - piperidine are together in 200 em3 abs. Benzene heated on the water bath for 3 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid.

   Then the hydrochloric acid extract is extracted with ether, with ice cooling with conc. Sodium hydroxide solution was added and the separated oil was taken up in ether. After the ether extracts have been dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



  The α-methyl-piperidino-acetic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide, boiling below 0.01 mm at 179-180, is obtained in a yield of 65'II / a of theory. Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids.

Claims (1)

PATENTAINTSPRUCH Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, d@a- dur ch gekennzeichnet, dass man eine Verbin dung der Formel EMI0001.0052 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit 2-lvIethyl-piperidin umsetzt. PATENTAIN CLAIM Process for the production of a new basic substituted fatty acid amide, d @ a- characterized by the fact that one is a compound of the formula EMI0001.0052 in which X denotes a reactive radical which is split off during the reaction, with 2-ivethylpiperidine. Das auf diese Weise erhaltene cc-11rIethyl-piperidino-essig- säure-N - [ 3-(2',4',6'-trimethyl-phenoxy) -propyl- 2]-methylamid bildet ein farbloses, unter 0,01 mm bei 179-180 siedendes Öl. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. The cc-11rIethyl-piperidino-acetic acid-N - [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide obtained in this way forms a colorless, less than 0.01 mm oil boiling at 179-180. The new amide will be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Halogenessig- säure-N- [3- (2',4', 6'-trimethyl-phenoxy)-propy l- 2]-methylamid mit. 2-@Tethyl-piperidin reagie ren lässt. SUBCLAIM: Process according to claim, characterized in that a haloacetic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propy 1-2] -methylamide is used. 2- @ Tethylpiperidine can react.
CH311686D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311686A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311686T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311686A true CH311686A (en) 1955-11-30

Family

ID=25735419

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311686D CH311686A (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) CH311686A (en)

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