CH240162A - 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
CH240162A
CH240162A CH240162DA CH240162A CH 240162 A CH240162 A CH 240162A CH 240162D A CH240162D A CH 240162DA CH 240162 A CH240162 A CH 240162A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
phenyl
piperidino
act
allowed
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 CH240162A publication Critical patent/CH240162A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basiseben Esters einer     1-Aryl-eyeloalkyl-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     Piperidinoäthanol    auf  eine Verbindung der Formel  
EMI0001.0006     
    worin X einen bei der Reaktion sich abspal  tenden Rest bedeutet, gegebenenfalls in Ge  genwart eines     Kondensationsmittels,    einwir  ken lässt.  



  Der     1-Phenyl-cyclopentyl-l-carbonsäure-          piperidino-äthanolester    bildet eine farblose  Flüssigkeit vom Siedepunkt     135-136     unter  0,15 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  12,9 Teilen     Piperidinoäthanol    in 50 Teilen  absolutem Benzol zu und erwärmt anschlie  ssend 2 Stunden zum Sieden. Man schüttelt  zweimal mit Wasser und einmal mit ver  dünnter Salzsäure aus.

   Die     vereinigten          wässrigen    Lösungen werden     ausgeäthert,    die  Base mit     Pottasche    in Freiheit gesetzt und in       Äthern    aufgenommen. Die ätherische Lö  sung wird mit Wasser gewaschen, über Pott  asche getrocknet und das Lösungsmittel ab  destilliert. Die neue     Verbindung    siedet bei  135-136<B>0</B> unter 0,15 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 piperidinoethanol is applied to a compound of the formula
EMI0001.0006
    where X is a radical which splits off during the reaction, optionally in the presence of a condensing agent, can be acted upon.



  The 1-phenyl-cyclopentyl-1-carboxylic acid piperidino-ethanol ester forms a colorless liquid with a boiling point of 135-136 below 0.15 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 12.9 parts of piperidinoethanol 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 ethers. The ethereal solution is washed with water, dried over pot ash and the solvent is distilled off. The new connection boils at 135-136 <B> 0 </B> below 0.15 mm. 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 basischen Esters einer 1 Aryl-cycloalkyl-l-eari)onsäure, dadurch gekennzeichnet, da.ss man Piperidino- ätha.nol auf eine Verbindung der Formel EMI0002.0007 worin X einen bei der Reaktion sieh abspal tenden Rest bedeutet, einwirken lässt. Der 1-Phenyl-eyelopentyl-l-carbonsäui-e- piperidinoätha,nolester bildet eine farblose Flüssigkeit vom Siedepunkt 135-136 unter 0,15 mm. Die neue Verbindung soll therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of a basic ester of a 1 aryl-cycloalkyl-l-earionic acid, characterized in that one piperidino-ethanol is based on a compound of the formula EMI0002.0007 where X is a residue that splits off during the reaction. The 1-phenyl-eyelopentyl-l-carbonsäui-e-piperidinoätha, nolester forms a colorless liquid with a boiling point 135-136 below 0.15 mm. The new compound should find therapeutic use. 1J \ TERA \ SPRt\CHh 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Piperidino- ii.t;lianol auf ein 1-Plienyl-cyelopentyl-l-car- honsäurehalogenid einwirken lässt. \?. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Piperidino- äthanol auf einen 1-Phenyl-cyclopenlyl-l- earbonsäureester einwirken lässt. 3. 1J \ TERA \ SPRt \ CHh 1. A method according to claim, characterized in that piperidino- ii.t; lianol is allowed to act on a 1-plienyl-cyelopentyl-1-carboxylic acid halide. \ ?. Process according to patent claim, characterized in that piperidinoethanol is allowed to act on a 1-phenyl-cyclopenlyl-1-carboxylic acid ester. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Piperidino- iithanol auf 1-Phenyl-cyelopenty 1-1-earbon- siiureanliydrid einwirken lässt. 4. Verfahren nach Patentanspruch, da durch gekenzeiehnet, dass man Piperidino- äthanol auf 1-Phenyl-cyclopentyl-l-earbon- saure einwirken lässt. 5. Verfahren nach Patentanspruch, da-; durch gekennzeichnet, dass man die Umset zung in Gegenwart eines Kondensationsmit tels vornimmt. A method according to patent claim, characterized in that piperidino-iithanol is allowed to act on 1-phenyl-cyelopenty 1-1-earbonic acid anhydride. 4. The method according to claim, since by gekenzeiehnet that piperidino ethanol is allowed to act on 1-phenyl-cyclopentyl-l-earbon acid. 5. The method according to claim, da-; characterized in that the implementation is carried out in the presence of a condensation agent.
CH240162D 1942-12-16 1942-12-16 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH240162A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH240162T 1942-12-16
CH234452T 1944-03-20

Publications (1)

Publication Number Publication Date
CH240162A true CH240162A (en) 1945-11-30

Family

ID=25727865

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240162D CH240162A (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) CH240162A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573015A (en) * 1947-12-24 1951-10-30 Geigy Ag J R Basic esters of 1-aryl-cyclopentene-(3)-1-carboxylic acids
US2704284A (en) * 1952-06-28 1955-03-15 Abbott Lab Therapeutic compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573015A (en) * 1947-12-24 1951-10-30 Geigy Ag J R Basic esters of 1-aryl-cyclopentene-(3)-1-carboxylic acids
US2704284A (en) * 1952-06-28 1955-03-15 Abbott Lab Therapeutic compounds

Similar Documents

Publication Publication Date Title
CH240162A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH242287A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH242245A (en) Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH242288A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240160A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH245908A (en) Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240163A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240164A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240167A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240165A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240168A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240166A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240161A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH245909A (en) Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.
DE652602C (en) Process for the production of condensation products
DE680182C (en) Process for the preparation of chlorides of polycarboxylic acids
CH234452A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH247926A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH247927A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH249042A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH242289A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH268459A (en) Process for the preparation of a basic ester.
CH268458A (en) Process for the preparation of a basic ester.
CH268453A (en) Process for the preparation of a basic ester.
CH269424A (en) Process for the preparation of a basic ester.