CH242245A - 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
CH242245A
CH242245A CH242245DA CH242245A CH 242245 A CH242245 A CH 242245A CH 242245D A CH242245D A CH 242245DA CH 242245 A CH242245 A CH 242245A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
cyclopentyl
ethylenediamine
act
phenyl
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 CH242245A publication Critical patent/CH242245A/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

Landscapes

  • 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

  

  Verfahren zur Darstellung eines     basischen        Amids    einer     1-Aryl-cycloalkyl-l-earbonsäure.       Gegenstand des vorliegenden Patentes     ist     ein Verfahren zur Darstellung eines basi  schen     Amids    einer     1-Aryl-cycloalkyl-l-car-          bonsäure.    Das Verfahren ist dadurch gekenn  zeichnet, dass man     N,N-Diäthyl-äthylendiamin     auf eine Verbindung der Formel  
EMI0001.0009     
    worin X 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-äthylamid    bildet eine farb  lose Flüssigkeit vom Siedepunkt 140-142   unter     0,088    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 ge  löst. Unter Rühren tropft man eine Lösung  von 11,6 Teilen     N,N-Diäthyl-äthylendiamin     in 50 Teilen absolutem Benzol zu und er  wärmt anschliessend 2     Stunden    zum Sieden.  Man schüttelt zweimal mit Wasser und ein  mal mit verdünnter Salzsäure aus.

   Die ver  einigten wässerigen Lösungen werden     ausge-          äthert,    die Base mit     Pottasche    in Freiheit ge  setzt und in     Aether        aufgenommen.    Die äthe  rische     Lösung    wird mit Wasser gewaschen,  über Pottasche     getrocknet    und das Lösungs  mittel     abdestilliert.    Die neue Verbindung sie  det bei 140-142  unter     0,0-3    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-cycloalkyl-1-carboxylic acid. The subject of the present patent is a method for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized in that N, N-diethyl-ethylenediamine is applied to a compound of the formula
EMI0001.0009
    where X is a radical which splits off during the reaction, optionally in the presence of a condensing agent, can be acted upon.



  The 1-phenyl-cyclopentyl-1-carboxylic acid ß-diethylamino-ethylamide forms a colorless liquid with a boiling point of 140-142 below 0.088 mm.



  The new compound should find therapeutic use. <I> Example: </I> 19 parts of 1-phenyl-cyclopentyl-1-carboxylic acid are converted into the acid chloride with thionyl chloride in the customary manner. and this dissolved in 200 parts of absolute benzene. A solution of 11.6 parts of N, N-diethyl-ethylenediamine in 50 parts of absolute benzene is added dropwise with stirring and it 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 is set free with potash and taken up in ether. The ethereal solution is washed with water, dried over potash and the solvent is distilled off. The new connection is below 0.0-3 mm at 140-142.

      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-eycloallryl-l-car- bonsäure, dadurch gekennzeichnet, dass man N,N-Diäthyl-äthylendiamin auf eine Verbin dung der Formel EMI0002.0007 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken lässt. Das 1-P'henyl-cyclopentyl-l-carbonsäure- ss-diäthylamino-äthylamid bildet eine farb lose Flüssigkeit vom Siedepunkt 140-142 unter 0,03 mm. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRÜCHE: 1. Claim: Process for the preparation of a basic amide of a 1-aryl-eycloallryl-l-carboxylic acid, characterized in that N, N-diethyl-ethylenediamine is applied to a compound of the formula EMI0002.0007 where X is a residue that splits off during the reaction, can act. The 1-phenyl-cyclopentyl-1-carboxylic acid ß-diethylamino-ethylamide forms a colorless liquid with a boiling point of 140-142 below 0.03 mm. The new compound should find therapeutic use. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthy l- äthylendiamin auf ein 1-P'henyl-cyclopentyl- 1-carbonsäurehalogenid einwirken lässt. 2. Verfahren nach- Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl < äthylendiamin auf einen 1-Pheny 1-cyclopen- tyl-l-carbonsäureester einwirken lässt. Process according to patent claim, characterized in that N, N-diethy l-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 <ethylenediamine is allowed to act on a 1-pheny-1-cyclopentyl-1-carboxylic acid ester. 3,. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-Diäthyl- äthylendiamin auf 1-Phenyl-cyclopentyl-l- carbonsäureanhydrid einwirken lässt. 4. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N,N-DiKthyl- äthylendiamin auf 1-P'henyl-cy clopentyl-l- carbonsäure einwirken lässt. 5. 3 ,. Process according to patent claim, characterized in that N, N-diethyl-ethylenediamine is allowed to act on 1-phenyl-cyclopentyl-1-carboxylic acid anhydride. 4. The method according to claim, characterized in that N, N-diethyl ethylenediamine is allowed to act on 1-phenyl-cyclopentyl-1-carboxylic acid. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Umset zung in Gegemvart .eines Kondensationsmit tels vornimmt. Method according to claim, characterized in that the implementation is carried out in the opposite of a condensation agent.
CH242245D 1944-03-20 1942-12-16 Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. CH242245A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH242245T 1944-03-20

Publications (1)

Publication Number Publication Date
CH242245A true CH242245A (en) 1946-04-30

Family

ID=4462857

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242245D CH242245A (en) 1944-03-20 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) CH242245A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573015A (en) * 1947-12-24 1951-10-30 Geigy Ag J R Basic esters of 1-aryl-cyclopentene-(3)-1-carboxylic acids
DE965324C (en) * 1955-01-19 1957-06-06 Cassella Farbwerke Mainkur Ag Process for the preparation of bromine-substituted cyclopentyl acetic acid amides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573015A (en) * 1947-12-24 1951-10-30 Geigy Ag J R Basic esters of 1-aryl-cyclopentene-(3)-1-carboxylic acids
DE965324C (en) * 1955-01-19 1957-06-06 Cassella Farbwerke Mainkur Ag Process for the preparation of bromine-substituted cyclopentyl acetic acid amides

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