CH245909A - Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents

Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.

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Publication number
CH245909A
CH245909A CH245909DA CH245909A CH 245909 A CH245909 A CH 245909A CH 245909D A CH245909D A CH 245909DA CH 245909 A CH245909 A CH 245909A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
ethylenediamine
dimethyl
phenyl
tri
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH245909A publication Critical patent/CH245909A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

      Terfahren    zur Darstellung eines basischen     Aids    einer     1-Aryl-eycloalkyl-l-carbonsäure.       Gegenstand des vorliegenden Zusatz  patentes     ist    ein Verfahren zur Darstellung  eines basischen     Amids    einer     1-Aryl-cyclo-          alkyl-l-carbonsäure.    Das     Verfahren    ist da  durch     gekennzeichnet,    dass man     N,N,

  N'-Tri-          äthyl-äthylendi.amin.    auf eine     Verbindung     der     Formel     
EMI0001.0014     
         worin    X einen bei der Reaktion sich abspal  tenden Rest bedeutet, gegebenenfalls in Ge  genwart     eines        Kondensationsmittels,        einwir-          ken    lässt.  



  Das 1-     (3',4'    -     Dimethyl    -     phenyl)    -     cyclo-          hegyl    -1-     carbons        äure-ss-        diäthylamino-diäthyl-          amid    bildet     eine    farblose Flüssigkeit vom       Siedepunkt    159-161  unter 0,04 mm.  



  Die neue     Verbindung    soll     therapeutische     Verwendung     finden.       <I>Beispiel:</I>  23,2 Teile     1-(3',4'-Dimethyl-phenyl)-cy-          clohexyl-l-carbonsäure    werden mit     Thionyl-          chlorid    in üblicher Weise in das Säure  chlorid übergeführt und dieses in 200 Teilen  absolutem Benzol gelöst. Unter Rühren tropft  man     eine    Lösung von 14,4 Teilen     N,N,N'-          Triäthyl-äthylendiamin    in 50     Teilen    absolu  tem Benzol zu und erwärmt     anschliessend    2  Stunden zum Sieden.

   Man     schüttelt    zweimal  mit Wasser und einmal mit     verdünnter    Salz  säure aus. Die vereinigten     wässrigen    Lösun  gen werden     ausgeäthert,    die Base mit Pott  asche in Freiheit gesetzt und in Äther auf  genommen. Die ätherische Lösung wird mit  Wasser gewaschen, über     Pottasche    getrock  net und das Lösungsmittel     abdestilliert.    Die  neue Verbindung siedet bei 159-161  unter  0,04 mm.  



  An Stelle des Säurechlorids können auch  andere     Halogenide    der     1-(3',4'-Dimethyl-          phenyl)-cyclohegyl-l-carbonsäure,    die Säure  selbst, ihre     Ester    oder ihr     Anhydrid    ver  wendet werden.



      Method for the preparation of a basic Aids of a 1-aryl-cycloalkyl-1-carboxylic acid. The subject of the present additional patent is a process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized by the fact that N, N,

  N'-tri-ethyl-ethylenediamine. to a compound of the formula
EMI0001.0014
         where X is a radical which splits off during the reaction, optionally in the presence of a condensing agent, can act.



  The 1- (3 ', 4' - dimethyl - phenyl) - cyclo-hegyl -1-carboxylic acid-s-diethylamino-diethyl amide forms a colorless liquid with a boiling point of 159-161 below 0.04 mm.



  The new compound should find therapeutic use. <I> Example: </I> 23.2 parts of 1- (3 ', 4'-dimethyl-phenyl) -cyclohexyl-l-carboxylic acid are converted into the acid chloride in the usual way with thionyl chloride and this is converted into Dissolved 200 parts of absolute benzene. A solution of 14.4 parts of N, N, N'-triethyl-ethylenediamine in 50 parts of absolute benzene is added dropwise with stirring and the mixture is then heated to boiling for 2 hours.

   It is extracted twice with water and once with dilute hydrochloric acid. The combined aqueous solutions are extracted with ether, the base is set free with pot ash and taken up in ether. The ethereal solution is washed with water, getrock net over potash and the solvent is distilled off. The new compound boils below 0.04 mm at 159-161.



  Instead of the acid chloride, other halides of 1- (3 ', 4'-dimethylphenyl) -cyclohegyl-1-carboxylic acid, the acid itself, its ester or its anhydride can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen Amids einer 1-Aryl-cycloalkyl-l-car- bonsäure, dadurch gekennzeichnet, dass man N,N,N'-Triäthyl-äthylendiamin auf eine Ver bindung der Formel EMI0002.0005 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken iässt. Das 1- (3',4' - Dimethyl - phenyl) PATENT CLAIM: Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that N, N, N'-triethyl-ethylenediamine is applied to a compound of the formula EMI0002.0005 where X denotes a residue that splits off during the reaction, allows action. The 1- (3 ', 4' - dimethyl - phenyl) - cyclo- hexyl -1- carbonsäure-ss- diäthylamino-diäthyl- amid bildet eine farblose Flüssigkeit vom Siedepunkt 159-161 unter 0,04 mm. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRüCHE 1. - Cyclo-hexyl -1-carboxylic acid-ss-diethylamino-diethyl amide forms a colorless liquid with a boiling point of 159-161 below 0.04 mm. The new compound should find therapeutic use. SUBCLAIMS 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N,N'-Tri- äthyl-äthylendiamin auf ein 1-(3',4'-Di- methyl - phenyl) - cyclohexyl -1- carbonsäure- halogenid einwirken lässt. 2. A method according to claim, characterized in that N, N, N'-tri-ethyl-ethylenediamine is allowed to act on a 1- (3 ', 4'-dimethyl-phenyl) -cyclohexyl-1-carboxylic acid halide. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, da,ss man N,N,N'-Tri- äthyl-äthylendiamin auf einen 1-(3',4'-Di- methyl -, phenyl) - cyclohexyl -1- carbonsäure- ester einwirken lässt. 3. Process according to patent claim, characterized in that N, N, N'-tri-ethyl-ethylenediamine is converted to a 1- (3 ', 4'-dimethyl-, phenyl) -cyclohexyl-1-carboxylic acid ester can act. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N,N'-Tri- äthyl-äthylendiamin auf 1-(3',4'-Dimethyl- phenyl) - cy elohexyl -1, carbonsäureanhydrid einwirken lässt. 4. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N,N'-Tri- äthyl-äthylendiamin auf 1-(3',4'-Dimethyl- phenyl)-cyclohexyl-l-carbonsänre einwirken lässt. Process according to patent claim, characterized in that N, N, N'-tri-ethyl-ethylenediamine is allowed to act on 1- (3 ', 4'-dimethyl-phenyl) -cy elohexyl-1, carboxylic anhydride. 4. The method according to claim, characterized in that N, N, N'-tri-ethyl-ethylenediamine is allowed to act on 1- (3 ', 4'-dimethyl-phenyl) -cyclohexyl-1-carboxylic acid. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Um setzung in Gegenwart eines Kondensations mittels vornimmt. Process according to claim, characterized in that the implementation is carried out in the presence of a condensation agent.
CH245909D 1942-12-16 1942-12-16 Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. CH245909A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH245909T 1942-12-16
CH242245T 1944-03-20

Publications (1)

Publication Number Publication Date
CH245909A true CH245909A (en) 1946-11-30

Family

ID=25728671

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245909D CH245909A (en) 1942-12-16 1942-12-16 Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH245909A (en)

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