CH311581A - Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number
CH311581A
CH311581A CH311581DA CH311581A CH 311581 A CH311581 A CH 311581A CH 311581D A CH311581D A CH 311581DA CH 311581 A CH311581 A CH 311581A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
halogen
fatty acid
substituted fatty
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 CH311581A publication Critical patent/CH311581A/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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  Verfahren zur Herstellung eines basisch substituierten     Fettsäure-          (2-halogen.6.methyl-anilids).            Gegenstand    des vorliegenden Patentes bil  det. ein Verfahren zur Herstellung eines neuen  basisch substituierten     Fettsäure-(2-halogen-6-          met.hyl-anilids),    welches dadurch gekennzeich  net, ist, dass man eine Verbindung der Formel  
EMI0001.0006     
    mit.     --hIethyl-piperidin    umsetzt. Die Umset  zung kann in An- oder Abwesenheit von     Lö-          sungs-    bzw. Verdünnungsmitteln und     Anlage-          f-imgska.talysatoren    erfolgen.

   Vorzugsweise       wird    wegen der     Leiehtflüchtigkeit    des     2-Me-          thy1-piperidins    unter     Druek    gearbeitet.     Als          Anlagerungskatalysatoren    benützt man vor  teilhaft     quaternäre        Ammoniumbasen,    wie z.     B.          Trimethylbenzylammoniumhydroxyd.     



  Das so erhaltene     ss-(2'-Methyl-piperidino)-          propionsäure-(2-chlor-6-met.hyl-anilid)    bildet  ein farbloses Kristallpulver; dessen Hydro  chlorid schmilzt bei 191-193 . Das neue       Anilid    soll als Lokalanästhetikum und als       Zwischenprodukt    zur Herstellung weiterer  Derivate Verwendung finden.  



       Beispiel:     Ein Gemisch von 20 Gewichtsteilen Acryl  säure-(2-chlor-6-methyl-anilid), 18 Gewichts-    teilen     2-Methy        1-piperidin    und einigen Tropfen       Trimethylbenzyla.mmoniumhydroxyd    wird im       Autoklaven    während 20 Stunden auf 145   erhitzt. Nach dem Erkalten wird durch die  Reaktionsmischung Wasserdampf     zwecks    Ent  fernung flüchtiger Anteile geleitet. Anschlie  ssend wird verdampft und der Rückstand aus       Pet.roläther    umkristallisiert..

   Man erhält so das       ss-        (2'-Methyl-piperidino)        -propionsäure-2-chlor-          6-methyl-anilid    als farbloses Kristallpulver.



  Process for the production of a basic substituted fatty acid (2-halogen.6.methyl-anilide). Subject of the present patent bil det. a process for the preparation of a new basic substituted fatty acid (2-halogen-6-met.hyl-anilids), which is characterized in that one is a compound of the formula
EMI0001.0006
    With. - methyl piperidine converts. The implementation can take place in the presence or absence of solvents or diluents and system f-imgska.talysatoren.

   Because of the volatility of 2-methy1-piperidine, it is preferable to work under pressure. As addition catalysts are used before some quaternary ammonium bases, such as. B. Trimethylbenzylammonium hydroxide.



  The ss- (2'-methyl-piperidino) -propionic acid- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless crystal powder; its hydrochloride melts at 191-193. The new anilide is to be used as a local anesthetic and as an intermediate for the production of other derivatives.



       Example: A mixture of 20 parts by weight of acrylic acid (2-chloro-6-methyl-anilide), 18 parts by weight of 2-methyl 1-piperidine and a few drops of trimethylbenzyl ammonium hydroxide is heated to 145 in an autoclave for 20 hours. After cooling, steam is passed through the reaction mixture for the purpose of removing volatile components. It is then evaporated and the residue is recrystallized from petroleum ether.

   The ss- (2'-methyl-piperidino) -propionic acid-2-chloro-6-methyl-anilide is thus obtained as a colorless crystal powder.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines basiseh substituierten Pettsäure-(2-halogen-6-methyl- anilids), dadurch gekennzeichnet, da.ss man eine Verbindung der Formel EMI0001.0042 mit 2-Methyl-piperidin umsetzt. Das so er haltene ss-(2'-Methyl-piperidino)-propionsäure- (2-chlor-6-methyl-anilid) ist ein farbloses Kri stallpulver; dessen Hydrochlorid schmilzt bei 191-193 . Es soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. PATENT CLAIM Process for the production of a basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is a compound of the formula EMI0001.0042 Reacts with 2-methyl-piperidine. The ss- (2'-methyl-piperidino) -propionic acid- (2-chloro-6-methyl-anilide) obtained in this way is a colorless crystal powder; its hydrochloride melts at 191-193. It is said to be used as a local anesthetic and as an intermediate product.
CH311581D 1952-02-25 1952-02-25 Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311581A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311581T 1952-02-25
CH306512T 1952-06-08

Publications (1)

Publication Number Publication Date
CH311581A true CH311581A (en) 1955-11-30

Family

ID=25735180

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311581D CH311581A (en) 1952-02-25 1952-02-25 Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).

Country Status (1)

Country Link
CH (1) CH311581A (en)

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