CH258202A - 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
CH258202A
CH258202A CH258202DA CH258202A CH 258202 A CH258202 A CH 258202A CH 258202D A CH258202D A CH 258202DA CH 258202 A CH258202 A CH 258202A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
ester
aryl
cycloalkyl
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 CH258202A publication Critical patent/CH258202A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Esters einer     1-Aryl-cycloalkyl-l-carbonsäure.       Gegenstand vorliegenden Patentes; ist ein  Verfahren zur Darstellung eines basischen  Esters einer     1-Aryl-cycloalkyl-l-carbonsäure.     Das Verfahren ist. dadurch gekennzeichnet,       da.ss        mann    einen reaktionsfähigen Ester von       1-(3',4'-Dimethyl-phenyl)-        cyclopenta-n-1-        car-          bonsäure-(ss-oxy-äthyl)-ester,    wie z. B. einen       lialogenwa"serstoff-,    Schwefelsäure- oder       Arylsulfonsäureester,        mitMorpholin    umsetzt.

    Die     erhaltene    neue Verbindung, der     Morpho-          linoäthylester    der     1-(3',4'-Dimethyl-phenyl)-          Cyelopentan-l-carbonsäure,    ist eine Base vom  Siedepunkt 162 bis 164  unter 0,05 mm  Druck, ihr Hydrochlorid     schmilzt    bei 156  bis 157 . Sie soll therapeutische Verwendung  finden.  



       Beispiel:     28 Teile aus     1-(3',4'-Dimethyl-phenyl)-          cyclopentan-l-carbonsäure-chlorid    und     Äthy-          lenchlorhydrin        erhaltener    1-(3',4'-Dimethyl       phenyl)-cyclopentan-1-carbonsäure-(ss-chlor-          ä.thyl)-@ester    werden in der Wärme mit 17,4  Teilen     Morpholin    umgesetzt. Das Gemisch  wird in     verdünnter'    Salzsäure gelöst und  durch     Au:ssehütteln        mit    Äther von geringen  Mengen von     Neutralteilen    befreit:.

   Aus der  sauren     wässrigen    Lösung wird hierauf durch  Zusatz von     konzentriertem        Ammoniak    der    basische Ester abgeschieden. Er wird in  Äther     aufgenommen,    die ätherische Lösung  mit Wasser gewaschen und getrocknet. Der  nach dem     Abdestillieren    des Äthers als  Rückstand erhaltene     Morpholinoäthylester     der     1-(3',4'-Dimethyl-phenyl)-cyclopentan-l-          carbonsäure    siedet bei 162 bis 164  unter  0,05 mm Druck.



  Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. Subject of the present patent; is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The procedure is. characterized in that da.ss mann a reactive ester of 1- (3 ', 4'-dimethyl-phenyl) - cyclopenta-n-1-carboxylic acid (ss-oxy-ethyl) ester, such as. B. a Lialogenwa "hydrogen, sulfuric acid or aryl sulfonic acid ester, is reacted with morpholine.

    The new compound obtained, the morpholine ethyl ester of 1- (3 ', 4'-dimethyl-phenyl) -cyelopentane-1-carboxylic acid, is a base with a boiling point of 162 to 164 under 0.05 mm pressure; its hydrochloride melts at 156 to 157. It should find therapeutic use.



       Example: 28 parts of 1- (3 ', 4'-dimethyl-phenyl) -cyclopentane-1-carboxylic acid chloride and ethylene chlorohydrin obtained 1- (3', 4'-dimethyl phenyl) -cyclopentane-1-carboxylic acid- (ss-chloro- ä.thyl) - @ esters are reacted with 17.4 parts of morpholine when heated. The mixture is dissolved in dilute hydrochloric acid and freed from small amounts of neutral parts by shaking with ether.

   The basic ester is then deposited from the acidic aqueous solution by adding concentrated ammonia. It is taken up in ether, the ethereal solution washed with water and dried. The morpholinoethyl ester of 1- (3 ', 4'-dimethyl-phenyl) -cyclopentane-1-carboxylic acid obtained as residue after distilling off the ether boils at 162 to 164 under 0.05 mm pressure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eins basischen Esters einer 1-Aryl-cycloalkyl-l-carbonsäure, dadurch gekennzeichnet, dass man einen re aktionsfähigen Ester von 1-(3',4'-Dimethyl- phenyl) -cyclopentan-1- carbonsäure -(ss - oxy- äthyl)-ester mit Morpholin umsetzt. Die er haltene neue Verbindung, der Morpholino- äthylester der 1-(3',4'-Dimethyl-phenyl) PATENT CLAIM: Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that a reactive ester of 1- (3 ', 4'-dimethyl-phenyl) -cyclopentane-1-carboxylic acid - ( ss - oxy - ethyl) ester is reacted with morpholine. The he received new compound, the morpholino ethyl ester of 1- (3 ', 4'-dimethyl-phenyl) -cy- clopentan-l-carbonsäure, ist eine Base vom Siedepunkt 162 bis. 164 unter 0,05 mm Druck; ihr Hydrochlorid schmilzt bei 1.56 bis l57 . UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass mann 1-(3',4'-Dimethyl- phenyl) - cyclopentan -1- carbonsäure - ss - halo- gen-äthyl)-ester mit Morpholin umsetzt. -cy- clopentane-1-carboxylic acid, is a base with a boiling point of 162 to. 164 under 0.05 mm pressure; its hydrochloride melts at 1.56 to 157. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that 1- (3 ', 4'-dimethylphenyl) - cyclopentane -1-carboxylic acid - ss - halogen-ethyl) ester is reacted with morpholine.
CH258202D 1944-03-20 1944-03-20 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH258202A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH250770T 1944-03-20
CH258202T 1944-03-20

Publications (1)

Publication Number Publication Date
CH258202A true CH258202A (en) 1948-11-15

Family

ID=25729483

Family Applications (1)

Application Number Title Priority Date Filing Date
CH258202D CH258202A (en) 1944-03-20 1944-03-20 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH258202A (en)

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