CH242287A - Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents

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

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Publication number
CH242287A
CH242287A CH242287DA CH242287A CH 242287 A CH242287 A CH 242287A CH 242287D A CH242287D A CH 242287DA CH 242287 A CH242287 A CH 242287A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
phenyl
methyl
act
cyclohegyl
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 CH242287A publication Critical patent/CH242287A/en

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Description

  

  Verfahren zur Darstellung eines basischen Esters einer     1-Aryl-cycloalhyl-l-carbonsäure.       Gegenstand des vorliegenden Zusatz  patentes     ist    ein Verfahren zur Darstellung       eines    basischen Esters     einer        1-Aryl-cyclo-          alkyl-l-carbonsäure.    Das Verfahren     ist    da  durch gekennzeichnet, dass man     Diäthyl-          aminoäthanol        auf    eine     Verbindung    der For  mel  
EMI0001.0012     
    worin X einen bei der Reaktion sich ab  spaltenden Rest bedeutet,

   gegebenenfalls in  Gegenwart eines     Kondensationsmittels,        ein-          wirken    lässt.  



  Der     1-(4'-Methyl-phenyl)-cyclohegyl-l-          carbonsäure-diäthylaminoäthanolester    bildet  eine farblose Flüssigkeit vom Siedepunkt 138  bis 140      unter    0,08 mm.  



  Die neue     Verbindung    soll therapeutische       Verwendung        finden.       <I>Beispiel:</I>  21,7 Teile     1-(4'-Methyl-phenyl)-cyclo-          hegyl-l-carbonsäure    werden mit     Thionyl-          chlorid    in üblicher Weise     in    das Säurechlorid  übergeführt     und    dieses in 200     Teilen    abso  lutem Benzol gelöst.

   Unter Rühren tropft  man eine     Lösung    von 11,7 Teilen     Diäthyl-          aminoäthanol    in 50 Teilen absolutem Benzol  zu und erwärmt anschliessend 2     Stunden    zum  Sieden.

   Man schüttelt zweimal mit Wasser  und     einmal    mit verdünnter Salzsäure     aus.     Die vereinigten     wässrigen    Lösungen werden       ausgeäthert,    die Base mit Pottasche in Frei  heit gesetzt     und        in         < Äther        aufgenommen.    Die  ätherische     Lösung    wird mit Wasser ge  waschen, über Pottasche getrocknet und das       Lösungsmittel        abdestilliert.    Die neue     Verbin-          dung    siedet bei 138-140      unter    0,08 mm.  



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



  Process for the preparation of a basic ester of a 1-aryl-cycloalhyl-1-carboxylic acid. The subject of the present additional patent is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized in that diethylaminoethanol is based on a compound of the formula
EMI0001.0012
    where X is a radical which splits off during the reaction,

   optionally in the presence of a condensing agent, allowed to act.



  The 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid diethylaminoethanol ester forms a colorless liquid with a boiling point of 138 to 140 below 0.08 mm.



  The new compound should find therapeutic use. <I> Example: </I> 21.7 parts of 1- (4'-methyl-phenyl) -cyclo- hegyl-1-carboxylic acid are converted into the acid chloride in the usual way with thionyl chloride and this is converted into the acid chloride in 200 parts Benzene dissolved.

   A solution of 11.7 parts of diethylaminoethanol 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 extracted with ether, 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 compound boils below 0.08 mm at 138-140.



  Instead of the acid chloride, it is also possible to use other halides of 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid, the acid itself, its ester or its anhydride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen -Esters einer 1-Aryl-cycloalkyl-l-car- Bonsäure, dadurch gekennzeichnet, dass man Diäthylaminoäthanol auf- eine Verbindung der Formel EMI0002.0007 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken lässt. Der 1- (4'-Methyl-phenyl) - cyclohegyl-l- carbonsäure-diäthyl-aminoäthanolester bildet eine farblose Flüssigkeit vom Siedepunkt 138 bis 140 unter 0,08 mm. Claim: Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-l-carboxylic acid, characterized in that diethylaminoethanol is based on a compound of the formula EMI0002.0007 where X is a residue that splits off during the reaction, can act. The 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid diethyl-aminoethanol ester forms a colorless liquid with a boiling point of 138 to 140 below 0.08 mm. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Diäthyl- aminoäthanol auf ein 1-(4'-Methyl-phenyl)- cyclohegyl-l-carbonsäurehalogenid einwirken lässt. 2. The new compound should find therapeutic use. SUBClaims 1. Method according to patent claim, characterized in that diethyl aminoethanol is allowed to act on a 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid halide. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Diäthyl- aminoäthanol auf einen 1-(4'-Methyl-phenyl)- cyclohegyl-l-carbonsäureester einwirken lässt. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Diäthyl- amiuoäthanol auf 1-(4'-Methyl-phenyl)-cyclo- hegyl-l-carbonsäureanhydrid einwirken lässt. 4. Process according to patent claim, characterized in that diethylaminoethanol is allowed to act on a 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid ester. 3. The method according to claim, characterized in that diethyl amiuoethanol is allowed to act on 1- (4'-methyl-phenyl) -cyclo-hegyl-l-carboxylic anhydride. 4th Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Diäthyl- aminoäthanol auf 1- (4'- Methyl - phenyl)- cyclohegyl-l-carbonsäure einwirken lässt. 5. Verfahren nach Patentanspruch; da durch gekennzeichnet, dass man die Umset zung in Gegenwart eines Kondensationsmit tels vornimmt. Process according to patent claim, characterized in that diethylaminoethanol is allowed to act on 1- (4'-methyl-phenyl) -cyclohegyl-1-carboxylic acid. 5. Method according to claim; as characterized in that the implementation is carried out in the presence of a condensation agent.
CH242287D 1942-12-16 1942-12-16 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH242287A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242287T 1942-12-16
CH234452T 1944-03-20

Publications (1)

Publication Number Publication Date
CH242287A true CH242287A (en) 1946-04-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH242287D CH242287A (en) 1942-12-16 1942-12-16 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH242287A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005973B (en) * 1953-06-26 1957-04-11 Henri Morren Process for the production of new spasmolytically effective basic esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005973B (en) * 1953-06-26 1957-04-11 Henri Morren Process for the production of new spasmolytically effective basic esters

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