CH242289A - 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
CH242289A
CH242289A CH242289DA CH242289A CH 242289 A CH242289 A CH 242289A CH 242289D A CH242289D A CH 242289DA CH 242289 A CH242289 A CH 242289A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
cycloalkyl
aryl
preparation
ester
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 CH242289A publication Critical patent/CH242289A/en

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Description

  

      Verfahren    zur Darstellung eines basischen Esters einer     1-Aryl-cycloalkyl-l-carbonsäure.       Gegenstand des vorliegenden Zusatzpaten  tes ist ein     Verfahren    zur     Darstellung    eines  basischen Esters einer     1-Aryl-cycloalkyl-l-          carbonsäure.    Das Verfahren ist dadurch ge  kennzeichnet, dass man ein     ss-Halogen-äthanol     auf eine Verbindung der Formel  
EMI0001.0008     
    worin     g    einen bei der Reaktion sich abspal  tenden Rest bedeutet, gegebenenfalls in Ge  genwart eines     Kondensationsmittels,

      einwir  ken lässt     und        anschliessend    den erhaltenen       Halogenalkylester    mit     Diäthylamin    umsetzt.  



  Der     1-Phenyl-cyclopentyl-l-carbonsäure-          diäthyl-aminoäthanolester    bildet eine farblose  Flüssigkeit vom Siedepunkt 112-115  unter  0,07 mm, sein     Hydrochlorid    schmilzt bei 145  bis 146 .    Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  38 Teile     1-Phenyl-cyclopentyl-l-carbon-          säure    werden mit     Thionylchlorid        in    üblicher  Weise in das Säurechlorid übergeführt und  dieses mit 16 Teilen     Äthylenchlorhydrin    in  150     Teilen        Pyridin    umgesetzt. Nach be  endeter Reaktion giesst man in Wasser, stellt  kongosauer     und        äthert    aus. Nach dem Wa  schen und Trocknen der Ätherlösung wird das  Lösungsmittel     abdestilliert    und der Rück  stand     imVakuum    fraktioniert.

   Der     1-Phenyl-          cyclopentyl-l-carbonsäure--ss-chloräthylester     siedet bei 110-115      unter    0,02 mm. 25 Teile  dieser Verbindung setzt man in der Wärme  mit 15     Teilen        Diäthylamin    um, nimmt nach  beendeter Reaktion     in    verdünnter Salzsäure  auf,

       äthert    aus und gewinnt aus der     wässrigen          Lösung    den basischen Ester durch Zugabe  von Pottasche und     Ausäthern.    Nach Waschen  und Trocknen der Ätherlösung wird das Lö-           sungsmittel        abdestilliert        und    der     Rückstand     im     Hochvakuum    fraktioniert. Die neue     Ver-          bindung    siedet bei 112-115  unter 0,07 mm.



      Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-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 an β-haloethanol is applied to a compound of the formula
EMI0001.0008
    where g denotes a radical which is split off during the reaction, optionally in the presence of a condensing agent,

      einwir ken and then reacting the haloalkyl ester obtained with diethylamine.



  The 1-phenyl-cyclopentyl-1-carboxylic acid diethyl aminoethanol ester forms a colorless liquid with a boiling point of 112-115 below 0.07 mm; its hydrochloride melts at 145 to 146. The new compound should find therapeutic use.



  <I> Example: </I> 38 parts of 1-phenyl-cyclopentyl-l-carboxylic acid are converted into the acid chloride with thionyl chloride in the usual way and this is reacted with 16 parts of ethylene chlorohydrin in 150 parts of pyridine. When the reaction has ended, it is poured into water, made Congo acidic and etherified. After washing and drying the ethereal solution, the solvent is distilled off and the residue is fractionated in vacuo.

   The 1-phenyl-cyclopentyl-1-carboxylic acid - ss-chloroethyl ester boils below 0.02 mm at 110-115. 25 parts of this compound are reacted with 15 parts of diethylamine in the heat, and when the reaction is complete it is taken up in dilute hydrochloric acid,

       ethers out and extracts the basic ester from the aqueous solution by adding potash and ethers. After washing and drying the ethereal solution, the solvent is distilled off and the residue is fractionated in a high vacuum. The new compound boils below 0.07 mm at 112-115.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen Esters einer 1-Aryl-cycloalkyl-l-car- bonsäure, dadurch gekennzeichnet, dass man ein f Halogenäthanol auf eine Verbindung der Formel . EMI0002.0015 worin X einen bei der Reaktion sich ab spaltenden Rest bedeutet, einwirken lässt und anschliessend den erhaltenen Halogenalkyl- ester mit Diäthylamin umsetzt. PATENT CLAIM: A process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that a halogenoethanol is applied to a compound of the formula. EMI0002.0015 where X is a radical which splits off during the reaction, allows it to act and then reacts the haloalkyl ester obtained with diethylamine. Der 1-Phenyl-cyclopentyl-l-carbonsäure- diäthyl-aminoäthanolester bildet eine farb lose Flüssigkeit vom Siedepunkt 112-115 unter 0,07 mm. sein Hydrochlorid schmilzt bei 145-146 . Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in Gegenwart eines Kondensationsmittels vor nimmt. The 1-phenyl-cyclopentyl-1-carboxylic acid diethyl aminoethanol ester forms a colorless liquid with a boiling point of 112-115 below 0.07 mm. its hydrochloride melts at 145-146. The new compound should find therapeutic use. SUBSTANTIAL CLAIM Process according to claim, characterized in that the reaction is carried out in the presence of a condensing agent.
CH242289D 1942-12-16 1942-12-16 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH242289A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242289T 1942-12-16
CH234452T 1944-03-20

Publications (1)

Publication Number Publication Date
CH242289A true CH242289A (en) 1946-04-30

Family

ID=25727875

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242289D CH242289A (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) CH242289A (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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