CH311585A - 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
CH311585A
CH311585A CH311585DA CH311585A CH 311585 A CH311585 A CH 311585A CH 311585D A CH311585D A CH 311585DA CH 311585 A CH311585 A CH 311585A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
halogen
fatty acid
preparation
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 CH311585A publication Critical patent/CH311585A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (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-          methvL-anilids),    welches dadurch gekennzeich  net. ist, dass man eine Verbindung der Formel  
EMI0001.0005     
    mit     2-Methyl-piperidin    umsetzt. Die     Umset-          zun@-,    kann in An- oder Abwesenheit von     Lö-          sungs-    bzw. Verdünnungsmitteln und Anlage  rungskatalysatoren erfolgen.

   Vorzugsweise  wird wegen der Leichtflüchtigkeit des     2-Methyl-          piperidins    unter Druck gearbeitet. Als Anlage  rungskatalysatoren benützt man vorteilhaft       quaternäre        Ammoniumbasen,    wie z. B.     Trime-          thvlbenzy@lammoniumhydroxyd.     



  Das so erhaltene     ss-(2-1Vlethyl-piperidino)-          hutt.ersäure-(2'-chlor-6'-met.hyl-anilid)    bildet  ein farbloses, bei 126-128  schmelzendes Kri  stallpulver. Das neue     Anilid    soll als Lokal  anästhetikum und als     Zwischenprodukt    zur       Herstellung    weiterer Derivate Verwendung  finden.  



  <I>Beispiel:</I>  Ein Gemisch von 13,5 Gewichtsteilen     Cro-          tonsäure-(2-chlor-6-methyl-anilid),    32 Ge-         wichtst.eilen        2-Methyl-piperidin    und einigen  Tropfen     Trimethylbenzylammoniumhydroxyd     wird im     Autoklaven    während 20 Stunden auf       145         erhitzt.    Nach dem Erkalten wird durch  die Reaktionsmischung Wasserdampf     zwecks     Entfernung flüchtiger Anteile geleitet,.

   An  schliessend wird verdampft und der Rückstand  aus     Petroläther        umkristallisiert.    Man erhält  so das     ss-(2-Methyl-piperidino)-buttersäure-          (2'-chlor-6'-methyl-anilid)    als farbloses, bei       126-128     schmelzendes     Kristallpulver.  



  Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). Subject of the present patent bil det. a process for the production of a new basic substituted fatty acid (2-halogen-6-methvL-anilide), which is marked thereby. is that you can get a compound of the formula
EMI0001.0005
    Reacts with 2-methyl-piperidine. The conversion can take place in the presence or absence of solvents or diluents and plant catalysts.

   Because of the volatility of 2-methylpiperidine, it is preferred to work under pressure. As plant approximately catalysts are used advantageously quaternary ammonium bases, such as. B. Trimethvlbenzy @ lammonium hydroxide.



  The ss- (2-1Vlethyl-piperidino) -hutt.ersäure- (2'-chloro-6'-methyl-anilide) obtained in this way forms a colorless crystal powder melting at 126-128. The new anilide is to be used as a local anesthetic and as an intermediate product for the production of other derivatives.



  <I> Example: </I> A mixture of 13.5 parts by weight of crotonic acid (2-chloro-6-methyl-anilide), 32 parts by weight of 2-methyl-piperidine and a few drops of trimethylbenzylammonium hydroxide is placed in the autoclave heated to 145 for 20 hours. After cooling, water vapor is passed through the reaction mixture to remove volatile components.

   It is then evaporated and the residue is recrystallized from petroleum ether. This gives the ss- (2-methyl-piperidino) -butyric acid- (2'-chloro-6'-methyl-anilide) as a colorless crystal powder melting at 126-128.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung -eines basisch substituierten Fettsäure-(2-hal-ogen-6-methyl- anilids), dadurch gekennzeichnet, d@ass man eine Verbindung der Formel EMI0001.0041 mit 2-Methyl-piperidin umsetzt. Das so erhal tene ss-(2'-Methyl-piperidino)-buttersäitre-(2'- ehlor-6'-methyl-anilid) ist ein farbloses, bei j 126-128 schmelzendes Kristallpulver. Es soll als Lokalanästhetikum und als Zwischenpro dukt Verwendung finden. PATENT CLAIM: A process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl anilide), characterized in that a compound of the formula EMI0001.0041 Reacts with 2-methyl-piperidine. The ss- (2'-methyl-piperidino) -butyric acid (2'-chloro-6'-methyl-anilide) obtained in this way is a colorless crystal powder that melts at j 126-128. It should be used as a local anesthetic and as an intermediate product.
CH311585D 1952-02-25 1952-02-25 Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311585A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311585T 1952-02-25
CH306512T 1952-06-08

Publications (1)

Publication Number Publication Date
CH311585A true CH311585A (en) 1955-11-30

Family

ID=25735184

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311585D CH311585A (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) CH311585A (en)

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