CH274728A - Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. - Google Patents

Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.

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Publication number
CH274728A
CH274728A CH274728DA CH274728A CH 274728 A CH274728 A CH 274728A CH 274728D A CH274728D A CH 274728DA CH 274728 A CH274728 A CH 274728A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
cyclopentene
phenyl
dimethylamino
preparation
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 CH274728A publication Critical patent/CH274728A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines basischen Derivates     einer          1-Aryl-eyclopenten-(3)-1-carbonsäure.            (Tegenstand    vorliegenden Patentes ist ein  Verfahren zur     Herstellung        Eines    basischen  Derivates einer     1-Aryl-cyclopenten-(3)-1-car-          bonsäure.    Das Verfahren     ist    dadurch ge  kennzeichnet, dass man eine Verbindung der  Formel  
EMI0001.0009     
    mit einer Verbindung der Formel  
EMI0001.0010     
    worin Z und Y zwei mit Ausnahme     eines    in  einem von ihnen enthaltenen Sauerstoffatom  sich bei der Reaktion abspaltende Reste be  deuten, umsetzt.  



  Die erhaltene neue Verbindung, der     1-          Phenyl-cyclopenten-    (3)     -j.-carbonsäiue-y-di-          methylamino-propylester,    siedet unter 0,12 mm  Druck     bei122-124 ;    ihr Hydrochlorid schmilzt  bei 122-123  (.aus     EssigesterMethanol).    Die  Verbindung soll therapeutische Verwendung  finden.  



  <I>Beispiel:</I>  20,6     Teile        1-Phenyl-cyclopenten-(3)-1-car-          bonsäurechlorid,    aus der Säure mit     Thionyl-          chlorid    dargestellt,     werden    in 250 Volum-    teilen absolutem Äther gelöst, unter Rühren  und guter Kühlung mit Kältemischung eine  Lösung von 11 Teilen     y-Dimethylamino-pro-          panol        in    50     Volumteilen    absolutem Äther zu  getropft, wobei man die     Temperatur        unter    0   hält,

   und das Ganze nach vollendeter Zugabe  2 Stunden bei Zimmertemperatur weiterge  rührt. Darauf schüttelt man etwa zweimal  mit     Wasser    und einmal mit     verdünnter        SaJz-          säure        aus,    stellt die vereinigten wässerigen  Lösungen mit     Pottaschelösung        alkalisch    und       äthert    sie aus.

   Die ätherische Lösung wird       rillt        Wasser        gewaschen,    über     Pottasche    ge  trocknet und das     Lösungsmittel        abdestilliert.     Die Base siedet unter 0,12 .mm Druck bei 122       bis        124 ;        ihr        Hydrochlorid        schmilzt    bei 122  bis 123  (aus     Essigester/Methanol).     



  Dieselbe Verbindung kann man auch  durch     Umsetzung    von     1-Phenyl-.eyclopenten-          (3)-1-carbonsäure-äthylester    mit     y-Dimethyl-          amino-propano1    in Gegenwart von etwas     Na-          triumverbindimg        dieses    Alkohols     sowie    auch  durch     Umsetzung    von     1-Phenyl-cyclopenten-          (3)

  -1-carbonsät-tre    mit     y-Dimethylamino-pro-          pylchlorid-hydrochlorid        mittels        Kaliumear-          bonat    herstellen.



  Process for the preparation of a basic derivative of a 1-aryl-eyclopenten- (3) -1-carboxylic acid. (The subject matter of the present patent is a process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. The process is characterized in that a compound of the formula
EMI0001.0009
    with a compound of the formula
EMI0001.0010
    wherein Z and Y are two radicals, with the exception of one oxygen atom contained in one of them, which are split off in the reaction.



  The new compound obtained, the 1-phenyl-cyclopentene- (3) -j.-carboxylic acid-y-dimethylamino-propyl ester, boils under 0.12 mm pressure at 122-124; its hydrochloride melts at 122-123 (.from ethyl acetate-methanol). The compound is intended to find therapeutic use.



  <I> Example: </I> 20.6 parts of 1-phenyl-cyclopentene- (3) -1-carboxylic acid chloride, prepared from the acid with thionyl chloride, are dissolved in 250 parts by volume of absolute ether, with stirring and good cooling with a cold mixture, a solution of 11 parts of y-dimethylamino-propanol in 50 parts by volume of absolute ether is added dropwise, keeping the temperature below 0,

   and the whole thing is stirred for 2 hours at room temperature after the addition is complete. It is then shaken out about twice with water and once with dilute acidic acid, the combined aqueous solutions are made alkaline with potash solution and etherified.

   The ethereal solution is washed with water, dried over potash and the solvent is distilled off. The base boils under 0.12 mm pressure at 122 to 124; its hydrochloride melts at 122 to 123 (from ethyl acetate / methanol).



  The same compound can also be obtained by reacting 1-phenyl-.eyclopenten- (3) -1-carboxylic acid ethyl ester with γ-dimethylamino-propano1 in the presence of some sodium compound of this alcohol and also by reacting 1-phenyl- cyclopentene (3)

  Prepare -1-carbonate with γ-dimethylamino propyl chloride hydrochloride using potassium carbonate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines basischen Derivates einer 1-Aryd-cyclopenten-(3)-1.,car- bonsäure, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 mit einer Verbindung der Formel CH. Y-CH_ CH= CH2 @T < CH, PATENT CLAIM: Process for the preparation of a basic derivative of a 1-Aryd-cyclopenten- (3) -1., Car- bononic acid, characterized in that a compound of the formula EMI0002.0001 with a compound of the formula CH. Y-CH_ CH = CH2 @T <CH, worin Z und V zwei mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sich bei der Reaktion abspaltende Reste be deuten, umsetzt. Die erhaltene neue Verbindung, der 1- Phenyl-cyclopenten- (3) s1-carbonsäure-y-di- methylamino-propylester, siedet unter 0,12 mm Druck , bei 122-124 ; ihr Hydrochlorid schmilzt bei 122-123 (aus Essigester/Methanol). UNTERANSPRÜCHE: 1. wherein Z and V are two radicals which are split off in the reaction, with the exception of an oxygen atom contained in one of them, converts. The new compound obtained, the 1-phenyl-cyclopentene- (3) s1-carboxylic acid-y-dimethylamino-propyl ester, boils under 0.12 mm pressure at 122-124; its hydrochloride melts at 122-123 (from ethyl acetate / methanol). SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 1-Phenyl- cyclopenten-(3)-1-carbonsäure-halogenid auf y-Dimethylamino-propanol einwirken lässt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen 1-Phe- nyl-.cyclopenten-(3)-1-carbonsäure-ester auf y-Dimethylamino-propanol einwirken lässt. 3. Process according to claim, characterized in that a 1-phenyl-cyclopentene- (3) -1-carboxylic acid halide is allowed to act on γ-dimethylamino-propanol. 2. The method according to claim, characterized in that a 1-phenyl-.cyclopenten- (3) -1-carboxylic acid ester is allowed to act on y-dimethylaminopropanol. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Salz der 1-Phenyl-.eyclopenten-(3) -1-carbonsäure mit einem reaktionsfähigen Ester des y-Dimethyl- amino,propanols umsetzt. Process according to patent claim, characterized in that a salt of 1-phenyl-.eyclopenten- (3) -1-carboxylic acid is reacted with a reactive ester of γ-dimethylamino, propanol.
CH274728D 1947-12-24 1947-12-24 Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. CH274728A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH271773T 1947-12-24
CH274728T 1947-12-24

Publications (1)

Publication Number Publication Date
CH274728A true CH274728A (en) 1951-04-15

Family

ID=25731319

Family Applications (1)

Application Number Title Priority Date Filing Date
CH274728D CH274728A (en) 1947-12-24 1947-12-24 Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH274728A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5206411A (en) * 1989-06-23 1993-04-27 Shell Oil Company Cured arylcyclobutene carboxylate ester compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5206411A (en) * 1989-06-23 1993-04-27 Shell Oil Company Cured arylcyclobutene carboxylate ester compositions

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