CH274731A - 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.

Info

Publication number
CH274731A
CH274731A CH274731DA CH274731A CH 274731 A CH274731 A CH 274731A CH 274731D A CH274731D A CH 274731DA CH 274731 A CH274731 A CH 274731A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
phenyl
cyclopentene
aryl
preparation
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 CH274731A publication Critical patent/CH274731A/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)
  • 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     Herstelhing    eines basischen  Derivates einer     1-Aryl-eyelopenten-(3)-1-car-          bonsäure.    Das Verfahren     ist        dadurch    gekenn  zeichnet, dass man eine Verbindung der  Formel  
EMI0001.0008     
    mit einer Verbindung der Formel  
EMI0001.0009     
    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-          Phenyl-eyclopenten-(3        )-1-carbonsäure-co-mor-          pholino-hexylester,    siedet unter 0,15 mm Druck  bei 165-171 ; ihr Hydrochlorid     schmilzt    bei  94-96  (aus     Essigester/Methanol).    Die Ver  bindung soll therapeutische     Verwendung     finden.  



  <I>Beispiel:</I>  20,6 Teile     1-Phenyl--cyelopenten-(3)-1-car-          bonsäure-chlorid,    aus der Säure mit     Thionyl-          chlorid    dargestellt, werden in 250 Volum-    teilen absolutem Äther gelöst,     unter    Rühren  und guter     Kühhmg    mit Kältemischung eine  Lösung von 19 Teilen     co-Morpholino-hexanol     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     IATasser    und  einmal mit verdünnter     Salzsäure    aus, stellt  die vereinigten wässerigen Lösungen mit Pott  aschelösung     alkalisch    und     äthert    sie aus.

   Die  ätherische Lösung wird mit Wasser gewa  schen, über Pottasche getrocknet     -und    das  Lösungsmittel     abdestIlliert.    Die Base siedet  unter 0,15 mm Druck bei     165-1710;    ihr     Hy-          drochlorid        schmilzt    bei     94-96     (aus     Essig-          ester/iVlethanol)    .  



  Dieselbe     Verbindung    kann man auch  durch     Umsetzung    von     1-Phenyl-cyelopenten-          (3)-1-carbonsäure-äthylester    mit     oo-1Vlorpho-          lino-hexanol    in Gegenwart von etwas     Na-          triumverbindimg    dieses     Alkohols    sowie auch  durch Umsetzung von     1-Phen@Tl-cylopenten-          (3)

  -1-earbonsäure    mit     co    -     Morpholino    -     hexyl-          chlorid-hydrochlorid    mittels     Kaliumcarbonat          herstellen.  



  Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. The subject of the present patent is a process for the preparation of a basic derivative of a 1-aryl-eyelopenten- (3) -1-carboxylic acid. The process is characterized in that a compound of the formula
EMI0001.0008
    with a compound of the formula
EMI0001.0009
    wherein Z and Y are two radicals, with the exception of an oxygen atom contained in one of them, which are split off in the reaction.



  The new compound obtained, the 1-phenyl-cyclopentene- (3) -1-carboxylic acid-co-morpholino-hexyl ester, boils under 0.15 mm pressure at 165-171; its hydrochloride melts at 94-96 (from ethyl acetate / methanol). The connection is intended to find therapeutic use.



  <I> Example: </I> 20.6 parts of 1-phenyl-cyelopenten- (3) -1-carboxylic acid chloride, prepared from the acid with thionyl chloride, are dissolved in 250 parts by volume of absolute ether , a solution of 19 parts of co-morpholino-hexanol in 50 parts by volume of absolute ether was added dropwise with stirring and good cooling with cold mixture, keeping the temperature below 0, and after the addition was complete, stirring was continued for 2 hours at room temperature.

   Then shake out about twice with IA water and once with dilute hydrochloric acid, make the combined aqueous solutions alkaline with pot ash solution and ether out them.

   The ethereal solution is washed with water, dried over potash and the solvent is distilled off. The base boils under 0.15 mm pressure at 165-1710; Their hydrochloride melts at 94-96 (from ethyl acetate / ethanol).



  The same compound can also be obtained by reacting 1-phenyl-cyelopenten- (3) -1-carboxylic acid ethyl ester with oo-1Vlorpholinohexanol in the presence of some sodium compound of this alcohol and also by reacting 1-Phen @ Tl -cylopenten- (3)

  Prepare -1-carboxylic acid with co - morpholino - hexyl chloride hydrochloride using potassium carbonate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines basischen Derivates einer 1-Aryl-cyclopenten-(3)-1-car- bonsäure, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 mit einer Verbindung der Formel EMI0002.0002 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, Claim: Process for the preparation of a basic derivative of a 1-aryl-cyclopenten- (3) -1-carboxylic acid, characterized in that a compound of the formula EMI0002.0001 with a compound of the formula EMI0002.0002 wherein Z and Y are two radicals which are split off in the reaction, with the exception of an oxygen atom contained in one of them. The new connection received, der 1- Phenyl- cyelopenten- (3) -1-carbonsäure-co-mor- pholino-hebylester, siedet unter 0,15 mm Druck bei 165-171 ; ihr Hydroehlorid schmilzt. bei cJ4-cJ6 (aus Essigester/AIethanol). UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 1-Phenvl- eyclopenten-(3)-1-.carbonsäure-halogenid auf co-1Vlorpholino-hexanol einwirken lässt. 2. the 1-phenyl-cyelopenten- (3) -1-carboxylic acid-co-morpholino-hebyl ester, boils under 0.15 mm pressure at 165-171; their hydrochloride melts. at cJ4-cJ6 (from ethyl acetate / ethanol). SUBClaims 1. The method according to claim, characterized in that a 1-phenyl-eyclopenten- (3) -1-.carboxylic acid halide is allowed to act on co-1Vlorpholino-hexanol. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen 1-Phe- nyl-cyclopenten-(3)-1-carbonsäure-ester auf w-Morpholino-hexanol einwirken lässt. 3. Verfahren nach Patentaaisprueh, da durch gekennzeichnet, dass man ein Salz der 1.-Phenyl-cwclopenten-(3) -1-carbonsäure mit einem reaktionsfähigen Ester des co-Morpho- lino-hexanols umsetzt. Process according to patent claim, characterized in that a 1-phenyl-cyclopentene- (3) -1-carboxylic acid ester is allowed to act on w-morpholino-hexanol. 3. The method according to Patentaaisprueh, characterized in that a salt of 1.-phenyl-cwclopenten- (3) -1-carboxylic acid is reacted with a reactive ester of co-morpholino-hexanol.
CH274731D 1947-12-24 1947-12-24 Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid. CH274731A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH271773T 1947-12-24
CH274731T 1947-12-24

Publications (1)

Publication Number Publication Date
CH274731A true CH274731A (en) 1951-04-15

Family

ID=25731322

Family Applications (1)

Application Number Title Priority Date Filing Date
CH274731D CH274731A (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) CH274731A (en)

Similar Documents

Publication Publication Date Title
CH274731A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
CH274728A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
CH274732A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
CH274729A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
CH274727A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
CH274730A (en) Process for the preparation of a basic derivative of a 1-aryl-cyclopentene- (3) -1-carboxylic acid.
DE897103C (en) Process for the preparation of 2-diphenylacetyl-1, 3-indanedione and its non-toxic metal salts
AT215993B (en) Process for the preparation of new 4-oxo-2- (haloalkyl) -2,3-dihydro- [benzo-1,3-oxazines]
AT258910B (en) Process for the preparation of benzo-dihydro-thiadiazine derivatives
AT203004B (en) Process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their salts
AT256839B (en) Process for the preparation of new substituted 1-Cyclopropylmethy-piperidinen
AT146504B (en) Process for the preparation of amides of pyrazine monocarboxylic acid.
AT358014B (en) METHOD FOR THE PRODUCTION OF NEW CARBOXY-BENZYLOXYPHENYL ACETIC ACIDS
AT200151B (en) Process for the preparation of new 3-sulfanilamido-6-substituted pyridazines
CH281947A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
DE861839C (en) Process for the preparation of threo-1- (4&#39;-nitrophenyl) -2-dichloroacetylamino-1, 3-dichloropropane
AT217647B (en) Process for the production of the new 16α-methylpregnan - 3α - ol - 11,20 - dione or its esters
CH329195A (en) Process for the preparation of aliphatic acid amides
CH280072A (en) Process for the preparation of a substance which lowers the level of prothrombin in the blood.
CH269085A (en) Process for the preparation of a new hydrazine compound.
CH501009A (en) 1-(5-nitro-2-thiazolyl)-2-oxo-imidazolidines - prepn
CH258203A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH265754A (en) Process for the preparation of a basic ether of a p-substituted benzhydrol.
CH297724A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH281977A (en) Process for the preparation of a polyarylethylene derivative.