CH269405A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269405A
CH269405A CH269405DA CH269405A CH 269405 A CH269405 A CH 269405A CH 269405D A CH269405D A CH 269405DA CH 269405 A CH269405 A CH 269405A
Authority
CH
Switzerland
Prior art keywords
ether
representation
compound
basic ether
formula
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
Priority claimed from GB15558/43A external-priority patent/GB585994A/en
Publication of CH269405A publication Critical patent/CH269405A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  <B>Verfahren zur Darstellung eines basischen Äthers.</B>    Gegenstand vorliegenden Patentes ist ein  Verfahren zur Darstellung eines basischen  Äthers. Das Verfahren ist dadurch gekenn  zeichnet, dass man eine Verbindung der  Formel  
EMI0001.0001     
    auf eine Verbindung der Formel  
EMI0001.0002     
    worin X und Y zwei reaktionsfähige, mit Aus  nahme eines in einem von ihnen enthaltenen       Sauerstoffatoms,    sich bei der Reaktion abspal  tende Reste bedeuten, einwirken lässt.    Die erhaltene neue Verbindung, der     n-Pro-          pyl-        cyclohexylinethyl    -     earbin-Lf-diäthylamino        -          äthyl-ätlier,    siedet bei 149-156  unter 11 mm  Druck.

   Sie soll therapeutische Verwendung  finden.    <I>Beispiel:</I>    Man suspendiert 2 Teile pulverisiertes       Natriumamid    in 50 Teilen absolutem Benzol,  tropft 8,5 Teile     n-Propyl-cyclohexylmethyl-          carbinol    zu Lind rührt 1 Stunde bei 60 . Dann  werden 8 Teile     f-Diäthylamino-äthylchlorid     zugefügt und das Ganze 8 Stunden unter         Rückfluss    erhitzt. Nach dem Abkühlen wird  mit     10 /oiger    Salzsäure ausgeschüttelt; die  salzsauren Auszüge werden mit     Kaliumkarbo-          nat    alkalisch gestellt und die ausgeschiedene  Base in Äther gesammelt.

   Die mit konzentrier  ter     Pottaschelösung    gewaschene und über     ge-          glühter    Pottasche getrocknete Ätherlösung  wird eingedampft und der Rückstand im Va  kuum destilliert, wobei der     n-Propyl-cyclo-          liexy        lmethyl-carbin-ss-diäthylamino-äthyl-äther          unter    11 mm Druck bei 149-156      übergeht.       Zum gleichen Endprodukt gelangt man,  auch, wenn man einen reaktionsfähigen Ester  des     n-Propy        1-cyclohexylmethyl-earbinols,    z. B.

    ein     Halogenid,    in Gegenwart     halogenwasser-          stoffbindender    Mittel mit     fl-Diäthylamino-          äthanol    zur Umsetzung bringt.



  <B> Method for the preparation of a basic ether. </B> The subject of the present patent is a method for the preparation of a basic ether. The process is characterized in that a compound of the formula
EMI0001.0001
    to a compound of the formula
EMI0001.0002
    wherein X and Y two reactive, with the exception of one oxygen atom contained in one of them, are radicals which split off during the reaction, can act. The new compound obtained, the n-propyl-cyclohexylinethyl-earbin-Lf-diethylamino-ethyl-ether, boils at 149-156 under 11 mm pressure.

   It should find therapeutic use. <I> Example: </I> 2 parts of powdered sodium amide are suspended in 50 parts of absolute benzene, 8.5 parts of n-propylcyclohexylmethylcarbinol are added dropwise to and the mixture is stirred at 60 for 1 hour. Then 8 parts of f-diethylaminoethyl chloride are added and the whole is refluxed for 8 hours. After cooling, it is extracted with 10% hydrochloric acid; the hydrochloric acid extracts are made alkaline with potassium carbonate and the base which has separated out is collected in ether.

   The ether solution, washed with concentrated potash solution and dried over glowed potash, is evaporated and the residue is distilled in vacuo, the n-propyl-cycloliexyimethyl-carbin-ß-diethylamino-ethyl ether under 11 mm pressure at 149 -156 passes. The same end product is obtained, even if a reactive ester of n-propy 1-cyclohexylmethyl-earbinol, eg. B.

    brings a halide, in the presence of hydrogen halide binding agents with fl-diethylamino ethanol to implement.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Äthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0033 auf eine Verbindung der Formel EMI0001.0034 worin g und Y zwei reaktionsfähige, mit Aus nahme eines in einem von ihnen enthaltenen Sauerstoffatoms, sich bei der Reaktion abspal tende Reste bedeuten, einwirken lässt. Die erhaltene neue Verbindung, der n-Pro- pyl- cyclohexylmethyl- carbin-l-diäthylamino - äthyl-äther, siedet bei 149-156 unter 11 mm Druck. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0033 to a compound of the formula EMI0001.0034 wherein g and Y two reactive, with the exception of one oxygen atom contained in one of them, are radicals which split off during the reaction, can act. The new compound obtained, the n-propyl-cyclohexylmethyl-carbin-1-diethylamino-ethyl ether, boils at 149-156 under 11 mm pressure.
CH269405D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269405A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269405T 1943-08-11
GB15558/43A GB585994A (en) 1943-09-22 1943-09-22 Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom

Publications (1)

Publication Number Publication Date
CH269405A true CH269405A (en) 1950-06-30

Family

ID=32110433

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269405D CH269405A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269405A (en)

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