CH306793A - Process for making a new salt. - Google Patents

Process for making a new salt.

Info

Publication number
CH306793A
CH306793A CH306793DA CH306793A CH 306793 A CH306793 A CH 306793A CH 306793D A CH306793D A CH 306793DA CH 306793 A CH306793 A CH 306793A
Authority
CH
Switzerland
Prior art keywords
acid
chloro
methyl
new salt
anilide
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 CH306793A publication Critical patent/CH306793A/en

Links

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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid

Description

  

      Verfahren    zur Herstellung eines neuen Salzes.         Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Salzes,    welches dadurch gekennzeichnet ist,  dass man     N-Pyrrolidinoessigsäure-('2#-chlor-6-          methyl-anilid)    mit     Fumarsäure    zur Reaktion  bringt. Man kann die Umsetzung in einem  Lösungsmittel, wie zum Beispiel Alkohol,  Äther, Benzol,     Dioxan,    Wasser,     Wasser-Al-          koholgemischen,    vornehmen.  



  Man kann zur Ausführung des erfindungs  gemässen Verfahrens auch so vorgehen, dass  man ein solches Salz des     N-Pyrrolidinoessig-          säure-        (2-chlor    - 6 -     methyl-anilides)    mit einem  solchen Salz der     Fumarsäure    zusammenbringt,  aus welchen sich durch Umsetzung inter  mediär das freie     N-Pyrrolidinoessigsäure-(2-          ehlor-6-methyl-anilid)    und die freie     Fumar-          säure    bilden.

   Das Reaktionsprodukt besteht  in diesem Falle aus zwei     Salzen;    je nach der  Löslichkeit und     Kristallisationstendenz    der  selben tritt das     N-Pyrrolidinoessigsäure-(2-          ehlor-6-methylanilid)    -     hydrogen-        fumarat    als  erstes oder als zweites     Kristallisat    auf.  



  Das so erhaltene     N-Pyrrolidinoessigsäiire-          (2-chlor    - 6 -     methyl-anilid)-hydrogen-fitmarat     bildet farblose Kristalle, die bei     2-28    bis     2i30        unter Zersetzung schmelzen. Das neue Salz  soll als Lokalanästhetikum verwendet werden.    <I>Beispiel:</I>  5 g     N-Pyrrolidinoessigsäure    - (2 - chlor -     6-          methyl-anilid)    in Äther werden mit einer  Lösung von     2.;3    g     Fumarsäure    in einem Al  kohol-Äthergemisch versetzt.

   Nach kurzer Zeit  tritt Kristallisation     ein.    Nach einiger Zeit  werden die gebildeten     Kristalle    abgesaugt, mit  Äther gewaschen und dann getrocknet. Man  erhält 7,2 g des bei     2i2$    bis     2230     unter Zer  setzung schmelzenden     N-Pyrrolidinoessigsäure-          (?-chlor-6-methyl-anilid)        -liydrogen-fumarates.  



      Process for making a new salt. The subject of the present patent is a process for the preparation of a new salt, which is characterized in that N-pyrrolidinoacetic acid - ('2 # -chloro-6-methyl-anilide) is reacted with fumaric acid. The reaction can be carried out in a solvent, such as, for example, alcohol, ether, benzene, dioxane, water, water-alcohol mixtures.



  To carry out the process according to the invention, one can also proceed in such a way that such a salt of N-pyrrolidinoacetic acid (2-chloro-6-methyl-anilides) is brought together with such a salt of fumaric acid, from which it is obtained by reaction the free N-pyrrolidinoacetic acid (2-chloro-6-methyl-anilide) and the free fumaric acid form.

   The reaction product in this case consists of two salts; Depending on the solubility and tendency to crystallize, N-pyrrolidinoacetic acid (2-chloro-6-methylanilide) hydrogen fumarate occurs as the first or second crystallizate.



  The N-pyrrolidinoacetic acid (2-chloro-6-methyl-anilide) -hydrogen fitmarate obtained in this way forms colorless crystals which melt at 2-28 to 2130 with decomposition. The new salt is intended to be used as a local anesthetic. <I> Example: </I> 5 g of N-pyrrolidinoacetic acid - (2 - chloro - 6 - methyl anilide) in ether are mixed with a solution of 2; 3 g of fumaric acid in an alcohol-ether mixture.

   Crystallization occurs after a short time. After some time, the crystals formed are filtered off with suction, washed with ether and then dried. 7.2 g of N-pyrrolidinoacetic acid (? -Chloro-6-methyl-anilide) -lydrogen fumarate, which melts at 2 1/2 to 2230 with decomposition, are obtained.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Salzes, dadurch gekennzeichnet, dass man N- Pyrrolidinoessigsäure- (2-chlor -P6 - methyl-ani- lid) mit Fiunarsäure zur Reaktion bringt. PATENT CLAIM Process for the production of a new salt, characterized in that N-pyrrolidinoacetic acid- (2-chloro-P6 - methyl-anilide) is reacted with fiunaric acid. Das resultierende N-Pyrrolidinoessigsäure- (2,chlor - 6 - methyl-anilid)-hydrogen-fLimarat bildet farblose, bei 228 bis 213ss unter Zer setzung schmelzende Kristalle; es soll als Lo kalanästhetikum verwendet werden. The resulting N-pyrrolidinoacetic acid- (2, chloro-6-methyl-anilide) -hydrogen-fLimarat forms colorless crystals which melt at 228 to 213ss with decomposition; it is intended to be used as a local anesthetic.
CH306793D 1955-04-30 1952-02-25 Process for making a new salt. CH306793A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH306793T 1955-04-30

Publications (1)

Publication Number Publication Date
CH306793A true CH306793A (en) 1955-04-30

Family

ID=4492946

Family Applications (1)

Application Number Title Priority Date Filing Date
CH306793D CH306793A (en) 1955-04-30 1952-02-25 Process for making a new salt.

Country Status (1)

Country Link
CH (1) CH306793A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2532306A1 (en) * 1982-08-27 1984-03-02 Pharmaton Sa BASIC ACETANILIDES, PROCESS FOR THEIR PREPARATION AND MEDICAMENTS CONTAINING THE SAME

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2532306A1 (en) * 1982-08-27 1984-03-02 Pharmaton Sa BASIC ACETANILIDES, PROCESS FOR THEIR PREPARATION AND MEDICAMENTS CONTAINING THE SAME

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