CH245908A - 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.

Info

Publication number
CH245908A
CH245908A CH245908DA CH245908A CH 245908 A CH245908 A CH 245908A CH 245908D A CH245908D A CH 245908DA CH 245908 A CH245908 A CH 245908A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
phenyl
diethyl
methyl
act
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 CH245908A publication Critical patent/CH245908A/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

Description

  

  Verfahren zur Darstellung eines basischen     Amids    einer     1-Aryl-cycloalhyl-l-earbonsäure.       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-Diäthyl-          N'-methyl-äthylendiami_n    auf eine Verbin  dung der Formel  
EMI0001.0010     
         worin.        g    einen bei der Reaktion sich abspal  tenden Rest bedeutet,

   gegebenenfalls in Ge  genwart eines     Kondensationsmittels,        einwir-          ken    lässt.  



  Das     1-Phenyl-cyclopentyl-l-carbonsäure-          ss-diäthylamino-äthylmethylamid    bildet eine  farblose Flüssigkeit vom Siedepunkt 138 bis  l.40  unter 0,05 mm.  



  Die neue Verbindung soll therapeutische  Verwendung finden. '    <I>Beispiel:</I>  19 Teile     1-Phenyl-cyclopentyl-l-carbon-          säure    werden mit     Thionylchlorid    in üblicher  Weise in das Säurechlorid übergeführt und  dieses in 200 Teilen absolutem Benzol gelöst.  Unter Rühren tropft man     eine    Lösung von  13 Teilen     N,N-Diäthyl-N'-methyl-äthylen-          diamin        in    50 Teilen absolutem Benzol zu und       erwärmt    anschliessend 2     Stunden    zum Sieden.

    Man     schüttelt    zweimal mit Wasser und ein  mal     mit        verdünnter    Salzsäure     aus.    Die ver  einigten     wässrigen        Lösungen    werden     ausge-          äthert,    die Base mit Pottasche.     in    Freiheit  gesetzt und in Äther aufgenommen.

   Die       ätherische    Lösung     wird    mit Wasser gewa  schen, über Pottasche getrocknet     und    das       Lösungsmittel        abdestilliert.    Die neue Ver  bindung siedet bei     138-140         unter    0,05 mm.  



  An Stelle des Säurechlorids können auch  andere     Halogenide    der     1-Phenyl-cyclopentyl-          1-carbonsäure,    die     Säure    selbst, ihre Ester  oder ihr     Anhydrid    verwendet werden.



  Process for the preparation of a basic amide of a 1-aryl-cycloalhyl-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 in that N, N-diethyl-N'-methyl-äthylendiami_n is based on a compound of the formula
EMI0001.0010
         wherein. g means a residue that is split off during the reaction,

   if necessary in the presence of a condensing agent, can act.



  The 1-phenyl-cyclopentyl-l-carboxylic acid ß-diethylamino-ethylmethylamide forms a colorless liquid with a boiling point of 138 to 1.40 below 0.05 mm.



  The new compound should find therapeutic use. Example: 19 parts of 1-phenyl-cyclopentyl-1-carboxylic acid are converted into the acid chloride with thionyl chloride in the customary manner and this is dissolved in 200 parts of absolute benzene. A solution of 13 parts of N, N-diethyl-N'-methyl-ethylenediamine in 50 parts of absolute benzene is added dropwise with stirring and the mixture is then heated to the boil for 2 hours.

    It is extracted twice with water and once with dilute hydrochloric acid. The combined aqueous solutions are etherified, the base with potash. set in freedom and taken up in ether.

   The ethereal solution is washed with water, dried over potash and the solvent is distilled off. The new connection boils below 0.05 mm at 138-140.



  Instead of the acid chloride, other halides of 1-phenyl-cyclopentyl-1-carboxylic acid, the acid itself, its ester or its anhydride can also 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-Diäthyl-N'-methyl-äthylendiamin auf eine Verbindung der Formel EMI0002.0006 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken lässt. Das 1-Phenyl-cyclopentyl-l-carbonsäure- ss-diäthylamino-äthylmethylamid bildet eine farblose Flüssigkeit vom Siedepunkt 138 bis 140 unter 0,05 mm. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRüCHE 1. Claim: Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that N, N-diethyl-N'-methyl-ethylenediamine is applied to a compound of the formula EMI0002.0006 where X is a residue that splits off during the reaction, can act. The 1-phenyl-cyclopentyl-1-carboxylic acid ß-diethylamino-ethylmethylamide forms a colorless liquid with a boiling point of 138 to 140 below 0.05 mm. The new compound should find therapeutic use. SUBCLAIMS 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl- N'-methyl-äthy lendiamin auf ein 1-Phenyl- cyclopentyl -1- carbonsäur ehalogenid einwir ken lässt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl- N'-methyl-äthylendiamin auf einen 1-Phenyl- cyclopentyl - 1 - carbonsäureester einwirken lässt. 3. Process according to claim, characterized in that N, N-diethyl-N'-methyl-ethylenediamine is allowed to act on a 1-phenyl-cyclopentyl-1-carboxylic acid halide. 2. The method according to claim, characterized in that N, N-diethyl-N'-methyl-ethylenediamine is allowed to act on a 1-phenyl-cyclopentyl - 1 - carboxylic acid ester. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl- N'-methyl-äthylendia,min auf 1-Phenyl-cy- clopenty 1-1- carbonsäureanhydrid einwirken lässt. 4. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl- N'-methyl-äthylendiamin auf 1-Phenyl-cy- clopentyl-l-carbonsä.ure einwirken lässt. 5. Process according to patent claim, characterized in that N, N-diethyl-N'-methyl-ethylenedia, min is allowed to act on 1-phenyl-cy- clopenty 1-1-carboxylic acid anhydride. 4. The method according to claim, characterized in that N, N-diethyl-N'-methyl-ethylenediamine is allowed to act on 1-phenyl-cyclopentyl-l-carboxylic acid. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Um setzung in Gegenwart eines Kondensations- mittels vornimmt. Process according to patent claim, characterized in that the reaction is carried out in the presence of a condensation agent.
CH245908D 1942-12-16 1942-12-16 Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. CH245908A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH245908T 1942-12-16
CH242245T 1944-03-20

Publications (1)

Publication Number Publication Date
CH245908A true CH245908A (en) 1946-11-30

Family

ID=25728670

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245908D CH245908A (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) CH245908A (en)

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