CH274727A - 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
CH274727A
CH274727A CH274727DA CH274727A CH 274727 A CH274727 A CH 274727A CH 274727D A CH274727D A CH 274727DA CH 274727 A CH274727 A CH 274727A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
dimethyl
diethylamino
phenyl
cyclopentene
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 CH274727A publication Critical patent/CH274727A/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)

Description

  

  Verfahren zur Herstellung eines basischen Derivates einer       1-Aryl-cyclopenten-(3)-1-carbonsäure.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines basischen  Derivates einer     1-Aryl-cyclopenten-(3)-1-car-          bonsäure.    Das Verfahren ist dadurch gekenn  zeichnet, dass man eine Verbindung der  Formel  
EMI0001.0004     
    mit einer     Verbindung    der Formel  
EMI0001.0006     
    worin Z und Y 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-          (3',4'-        Dimethyl,        phenyl)    -     cyclopenten    - (3)     -1-          earbonsäure-ss-diäthylamino-äthylester,    siedet  unter 0,1 mm Druck bei 126-127 ; ihr     Hy-          droehlorid    schmilzt bei 166-167 . Die Ver  bindung soll therapeutische Verwendung  finden.  



  <I>Beispiel:</I>       \?3,4    Teile     1-(3',4'-Dimethyl-pheni>1)-eyelo-          penten-(3)-1-carbonsätire-chlorid,    aus der  Säure mit     Thionylchlorid        dargestellt,    werden  in 250     Volumteilen        abs.    Äther gelöst, unter    Rühren und guter Kühlung mit Kälte  mischung eine Lösung von 12 Teilen     Diäthy        1-          aminoäthanol    in 50     Volumteilen    absolutem  Äther     zugetropft,    wobei man die Temperatur  unter 0  hält,

       und    das Ganze nach vollendeter  Zugabe 2 Stunden bei Zimmertemperatur       weitergerührt.    Darauf schüttelt man etwa  zweimal mit Wasser     imd    einmal mit verdünn  ter     Salzsäure    aus, stellt die vereinigten wässe  rigen Lösungen     mit        Pottaschelösungalkalisch     und     äthert    sie aus.

   Die ätherische     Lösung     wird     mit        Wasser    gewaschen, über Pottasche  getrocknet und das Lösungsmittel     abdestil-          liert.    Die Base siedet unter 0,1 mm Druck bei  126-127 ; ihr Hydrochlorid schmilzt bei 166       bis    167 .

           Dieselbe    Verbindung kann man auch  durch Umsetzung von 1- (3',4' -     Dimethyl-          phenyl)        -cyclopenten-    (3) -1-     carbonsäure-äthyl-          ester    mit     Diäthylaminoäthanal    in Gegenwart  von etwas     Natriumverbindung    dieses     Alkohols     sowie auch durch Umsetzung von     1-(3',4'-Di-          methyl-phenyl)        -cyclopenten-    (3)

       -1-carbonsäure     mit     f-Diäthylamino-äth3Tlchlorid-hy        ärochlorid          mittels        Kaliumcarbonat    herstellen.



  Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. The present patent is a process for the preparation of a basic derivative of a 1-aryl-cyclopenten- (3) -1-carboxylic acid. The process is characterized in that a compound of the formula
EMI0001.0004
    with a compound of the formula
EMI0001.0006
    wherein Z and Y are two radicals, with the exception of an oxygen atom contained in one of them, which are split off during the reaction.



  The new compound obtained, the 1- (3 ', 4'-dimethyl, phenyl) - cyclopentene - (3) -1-carboxylic acid-ss-diethylamino-ethyl ester, boils under 0.1 mm pressure at 126-127; its hydrochloride melts at 166-167. The connection is intended to find therapeutic use.



  <I> Example: </I> \? 3.4 parts of 1- (3 ', 4'-dimethyl-pheni> 1) -eyelopenten- (3) -1-carbonate chloride, from the acid with thionyl chloride are shown in 250 parts by volume abs. Ether dissolved, with stirring and good cooling with cold mixture, a solution of 12 parts diethy 1- aminoethanol in 50 parts by volume of absolute ether was added dropwise, keeping the temperature below 0,

       and the whole thing is stirred for a further 2 hours at room temperature after the addition is complete. Then it is extracted about twice with water and once with dilute hydrochloric 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 at 126-127 under 0.1 mm pressure; its hydrochloride melts at 166 to 167.

           The same compound can also be obtained by reacting 1- (3 ', 4' -dimethylphenyl) -cyclopenten- (3) -1-carboxylic acid ethyl ester with diethylaminoethanol in the presence of some sodium compound of this alcohol and also by reacting 1 - (3 ', 4'-Dimethyl-phenyl) -cyclopentene- (3)

       Prepare -1-carboxylic acid with f-diethylamino-eth.3-chloride hydrochloride using potassium carbonate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines basischen Derivates einer 1- Aryl - cyclopenten - (3) -1- carbonsäure, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 mit einer Verbindung der Formel EMI0002.0003 worin Z Lind Y zwei mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sich bei der Reaktion abspaltende Reste be deuten, umsetzt. Die erhaltene neue Verbindung, PATENT CLAIM: Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid, characterized in that a compound of the formula EMI0002.0001 with a compound of the formula EMI0002.0003 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 connection received, der 1- (3',4'-Dimethyl-phenyl) - cyclopenten- (3) -1 carbonsäure-ss-diäthylamino-äthylester, siedet -unter 0,1 mm Druck bei 126-127 ; ihr Hy- drochlorid schmilzt bei 166-167 . UNTERANSPRÜCHE: 1. the 1- (3 ', 4'-dimethyl-phenyl) -cyclopenten- (3) -1-carboxylic acid-ss-diethylamino-ethyl ester, boils -under 0.1 mm pressure at 126-127; its hydrochloride melts at 166-167. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 1-(j ,4'- Dimethyl..phenyl) -cycl.openten-(3)-1; carbon- säurehalogenid auf ss-Diäthylamino-äthanol einwirken lässt. Process according to patent claim, characterized in that a 1- (j, 4'-dimethyl..phenyl) -cycl.openten- (3) -1; carboxylic acid halide can act on s-diethylamino-ethanol. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen 1-(3',4'- Dimethyl,-phenyl)-cyelopenten-(3) -1z-,carbon- säure-ester auf ss-Diäthylamino-äthanol ein wirken lässt. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Salz der 1-(3',4'-Dimethyl-phenyl) -rcyclopenten-(3)-1- carbonsäure mit einem reaktionsfähigen Ester des ss-Diäthylamino-äthanols umsetzt. 2. The method according to claim, characterized in that a 1- (3 ', 4'-dimethyl, -phenyl) -cyelopenten- (3) -1z-, carboxylic acid ester act on s-diethylamino-ethanol leaves. 3. The method according to claim, characterized in that a salt of 1- (3 ', 4'-dimethyl-phenyl) -rcyclopenten- (3) -1-carboxylic acid is reacted with a reactive ester of s-diethylamino-ethanol.
CH274727D 1947-12-24 1947-12-24 Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. CH274727A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH271773T 1947-12-24
CH274727T 1947-12-24

Publications (1)

Publication Number Publication Date
CH274727A true CH274727A (en) 1951-04-15

Family

ID=25731318

Family Applications (1)

Application Number Title Priority Date Filing Date
CH274727D CH274727A (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) CH274727A (en)

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