CH311627A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

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

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Publication number
CH311627A
CH311627A CH311627DA CH311627A CH 311627 A CH311627 A CH 311627A CH 311627D A CH311627D A CH 311627DA CH 311627 A CH311627 A CH 311627A
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 CH311627A publication Critical patent/CH311627A/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 Fettsäure.       (2-halogen-6-methyl-auilids).       Gegenstand des vorliegenden Patentes bil  det ein     Verfahren    zur Herstellung eines neuen       basisch    substituierten     Fettsäure-(2-halogen-6-          methyl-an.ilids),    welches dadurch gekennzeich  net ist, dass man eine Verbindung der Formel  
EMI0001.0007     
    in welcher X einen reaktionsfähigen, während  der Reaktion sich abspaltenden Rest bedeutet,  mit     2-1lleth.-#>1-piperidin    umsetzt.  



  Der Rest. X kann in einem Halogenatom  oder einem sonstigen für den     Austausch    gegen  den basischen Rest geeigneten reaktionsfähi  gen     Substituenten,    wie z. B. einer     Alky1sul-          fonyIoxy-    oder     Arylsulfonyloxygruppe,    beste  ,     hen.    Der Austausch der Gruppe X gegen den       2-llethyl-piperidinrest    erfolgt z.

   B. durch     ein-          faelies    Erwärmen mit     2-IVlethyl-piperid'in    ge  gebenenfalls in Gegenwart eines basisch re  agierenden Kondensationsmittels oder von     2-          Methyl-piperidin    im     Überschuss.    Das ss-(2  llethyl-piperidino)-propionsäure=(2'-ehlor-6'  methyl-anilid) ist ein farbloses Kristallpulver.  Das Hydrochlorid der Base schmilzt bei<B>191</B>  bis 193 .  



  Das neue     Anilid    soll als Lokalanästhetikum  und als     Zwischenprodukt    zur     Herstellung    wei  terer Derivate Verwendung finden.    <I>Beispiel:</I>  29 Gewichtsteile     ss-Chlor-propionsäure-(2-          chlor-6-methyl-anilid)    (gewonnen durch Um  setzen von     2-Chlor-6-methyl-anilin    mit     ss-Chlor-          propionyl-chlorid    in Gegenwart von Natrium  acetat,     Schmp.    109-112 ) werden in 80 Ge  wichtsteilen Äthanol     suspendiert    und mit. 37  Gewichtsteilen     2-Methyl-piperidin    versetzt.

   Die  Temperatur steigt dabei leicht an und ein  grosser Teil des     Reaktionsgemisches    geht. in  Lösung. Nun wird während 4 Stunden bei       Zimmertemperatur    gerührt und dann einige  Stunden bei 65-75 . Eine Probe mit Wasser  und nachfolgend mit verdünnter     Salzsäure     versetzt, ergibt wieder Lösung des ausgefalle  nen Niederschlages. Mit Wasserdampf     wird     hierauf der Alkohol und das überschüssige       2-3lethyl-piperidin    abgeblasen und nach dem  Erkalten das zurückbleibende Öl in Äther auf  genommen. Nach dem Trocknen der ätheri  schen Lösung und Verjagen des Lösungsmit  tels verbleibt ein farbloses Kristallpulver.

   Man  erhält. 36 Gewichtsteile reines     ss-(2-Methyl-          piperidino)    -     propionsäure    - (2'-     chlor-6'-        methyl-          anilid).    Die Umsetzung mit     2-1lllethyl-piperidin     kann auch in Benzol stattfinden.



  Process for the production of a new basic substituted fatty acid. (2-halogen-6-methyl-auilids). The subject of the present patent forms a process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-an.ilids), which is characterized in that a compound of the formula
EMI0001.0007
    in which X denotes a reactive radical which is split off during the reaction, with 2-1lleth .- #> 1-piperidine.



  The radical. X can be in a halogen atom or other suitable reactive substituents for replacement with the basic radical, such as. B. an alky1sulfonyIoxy or arylsulfonyloxy group, best hen. The exchange of the group X against the 2-llethyl-piperidine radical takes place, for.

   B. by simple heating with 2-methyl-piperid'in ge optionally in the presence of a basic re acting condensing agent or of 2-methyl-piperidine in excess. The ss- (2 llethyl-piperidino) -propionic acid = (2'-chloro-6 'methyl-anilide) is a colorless crystal powder. The base hydrochloride melts at <B> 191 </B> to 193.



  The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 29 parts by weight of ss-chloro-propionic acid (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with s-chloro-propionyl- chloride in the presence of sodium acetate, melting point 109-112) are suspended in 80 parts by weight of ethanol and mixed with. 37 parts by weight of 2-methylpiperidine are added.

   The temperature rises slightly and a large part of the reaction mixture leaves. in solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65-75. A sample with water and then mixed with dilute hydrochloric acid results in a solution of the precipitate. The alcohol and the excess 2-3lethyl-piperidine are then blown off with steam and, after cooling, the remaining oil is taken up in ether. After the ethereal solution has dried and the solvent has been chased away, a colorless crystal powder remains.

   You get. 36 parts by weight of pure ss- (2-methylpiperidino) propionic acid - (2'-chloro-6'-methyl anilide). The reaction with 2-1lllethylpiperidine can also take place in benzene.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-a.nilicls), dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 in weleher X einen reaktionsfähigen, -während der Reaktion sich abspaltenden Rest bedeutet, mit 2-iUleth@rl-piperidin umsetzt. Das auf diese Weise erhaltene ss-(2-Methyl-piperidino)-pro- pionsäure-(2'-ehlor-6'-methvl-anilid) bildet ein farbloses Kristallpulver. PATENT CLAIM Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-a.nilicls), characterized in that a compound of the formula EMI0002.0001 in which X is a reactive radical which is split off during the reaction and reacts with 2-iUleth @ rl-piperidine. The ss- (2-methyl-piperidino) -propionic acid- (2'-chloro-6'-methyl anilide) obtained in this way forms a colorless crystal powder. Das Hy droehlorid der Base sehmilzt bei 191-193 . Das neue Anilid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. <B>UNTERANSPRUCH:</B> Verfahren nach Patentansprueh, dadureh gekennzeiehnet, dass man ein ss-Halogen-pro- pionsäure-(2-ehlor-6-methyl-anilid) mit 2-lle- thyl-piperidin reagieren lässt. The hydrochloride of the base melts at 191-193. The new anilide is to be used as a local anesthetic and as an intermediate product. <B> SUBCLAIM: </B> Process according to patent claim, characterized in that an β-halo-propionic acid (2-chloro-6-methyl-anilide) is allowed to react with 2-l-ethyl-piperidine.
CH311627D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311627A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311627T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311627A true CH311627A (en) 1955-11-30

Family

ID=25735360

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311627D CH311627A (en) 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Country Status (1)

Country Link
CH (1) CH311627A (en)

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