CH242288A - 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.

Info

Publication number
CH242288A
CH242288A CH242288DA CH242288A CH 242288 A CH242288 A CH 242288A CH 242288D A CH242288D A CH 242288DA CH 242288 A CH242288 A CH 242288A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
piperidino
cyclopentyl
propanol
act
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 CH242288A publication Critical patent/CH242288A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Description

       

      Verfahren    zur Darstellung eines     basiseben        Esters    einer     1-Aryl-eyeloalkyl-l-earbonsäure.       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     y-Piperidino-          propanol    auf eine     Verbindung    der Formel  
EMI0001.0012     
    worin X einen bei der Reaktion sich abspal  tenden Rest bedeutet,

   gegebenenfalls in Ge  genwart     eines    Kondensationsmittels,     ein-          wirken    lässt.  



  Der     1-Phenyl-cyclopentyl-l-carbonsäure-          y-piperidino-propanolester    bildet eine farb  lose Flüssigkeit vom Siedepunkt l45-147   unter 0,25 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 gelöst.  Unter Rühren tropft man     eine        Lösung    von  14,3 Teilen     y-Piperidino-propanol    in 50 Tei  len absolutem Benzol zu     und    erwärmt an  schliessend 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 Freiheit gesetzt und in  Äther aufgenommen. Die ätherische     Lösung     wird mit Wasser gewaschen, über Pottasche  getrocknet und das Lösungsmittel     abdestil-          liert.    Die neue     Verbindung    siedet bei 145 bis  147" unter 0,25 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 ester of a 1-aryl-eyeloalkyl-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 y-piperidino-propanol is applied to a compound of the formula
EMI0001.0012
    where X is a residue that splits off during the reaction,

   optionally in the presence of a condensing agent, can act.



  The 1-phenyl-cyclopentyl-1-carboxylic acid y-piperidino-propanol ester forms a colorless liquid with a boiling point of 145-147 below 0.25 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 is dissolved in 200 parts of absolute benzene. A solution of 14.3 parts of γ-piperidino-propanol 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 released 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 joint boils below 0.25mm at 145 to 147 ".



  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 Esters einer 1-Aryl-cycloalkyl-l-car- bonsäure, dadurch gekennzeichnet, dass. man y-Piperidino-propanol auf eine Verbindung der Formel EMI0002.0009 worin X einen bei der Reaktion sich abspal- tenden.Rest bedeutet, einwirken lässt. Claim: Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that y-piperidino-propanol is applied to a compound of the formula EMI0002.0009 where X means a residue that is split off during the reaction, can act. Der 1-Phenyl-cyclopentyl-l-carbonsäure- y-piperidino-propanolestex bildet. eine farblose Flüssigkeit vom Siedepunkt 145-147 unter 0,25 mm. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRÜUCRE : 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man y-Piperidino- propanol auf ein 1-Phenyl-cyclopentyl-l-car- bonsäurehalogenid einwirken lässt. 2. The 1-phenyl-cyclopentyl-l-carboxylic acid y-piperidino-propanolestex forms. a colorless liquid with a boiling point of 145-147 below 0.25 mm. The new compound should find therapeutic use. SUBClaims: 1. Process according to claim, characterized in that y-piperidino-propanol is allowed to act on a 1-phenyl-cyclopentyl-1-carboxylic acid halide. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man y-Piperidino- propanol auf einen 1-Phenyl-cyclopentyl-l- carbonsäureester einwirken lässt. 3. Verfahren nach Patentanspruch, da-; durch gekennzeichnet, dass man y-Piperidino= propanol auf 1-Phenyl-cyclopentyl-l-carbon- säureanhydrid einwirken lässt. 4. Process according to patent claim, characterized in that y-piperidino-propanol is allowed to act on a 1-phenyl-cyclopentyl-1-carboxylic acid ester. 3. The method according to claim, da-; characterized in that y-piperidino = propanol is allowed to act on 1-phenyl-cyclopentyl-1-carboxylic acid anhydride. 4th Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man y-Piperdino- propanol auf 1-Pb.enyl-cyclopentyl-l-carbon- säure. 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 y-piperdino-propanol is converted to 1-Pb.enyl-cyclopentyl-1-carboxylic acid. can act. 5. The method according to claim, characterized in that the implementation is carried out in the presence of a condensation agent.
CH242288D 1942-12-16 1942-12-16 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH242288A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242288T 1942-12-16
CH234452T 1944-03-20

Publications (1)

Publication Number Publication Date
CH242288A true CH242288A (en) 1946-04-30

Family

ID=25727874

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242288D CH242288A (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) CH242288A (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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