CH269406A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269406A
CH269406A CH269406DA CH269406A CH 269406 A CH269406 A CH 269406A CH 269406D A CH269406D A CH 269406DA CH 269406 A CH269406 A CH 269406A
Authority
CH
Switzerland
Prior art keywords
ether
representation
compound
cyclohexyl
basic ether
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 CH269406A publication Critical patent/CH269406A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Äthers.    Gegenstand vorliegenden Patentes ist ein  Verfahren zur Darstellung eines basischen       -Äthers.    Das Verfahren ist dadurch gekenn  zeichnet, dass man eine Verbindung der  5 Formel  
EMI0001.0002     
    auf eine Verbindung der Formel  
EMI0001.0003     
    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     Cyclo-          hexyl-cy        clohexylmethyl-carbin-f-diäthylamino-          äthyl-äther,    siedet bei 159-163o unter 0,1 mm  Druck. Sie soll therapeutische Verwendung  finden.  



       Beispiel:     Man suspendiert 1,3 Teile pulverisiertes       Natriumamid    in 50 Teilen absolutem Benzol,  tropft 6,5 Teile     Cyclohexyl-cyclohexylmethyl-          carbinol,    zugänglich aus     Cyclohexylmethyl-          magnesiumbromid    und     Cyclohexylaldehyd,    zu  und rührt, 1 Stunde bei 60 . Dann werden  6 Teile     ss-Diäthylamino-äthy        lchlorid    zugefügt  und das Ganze 8 Stunden unter     Rückfluss       erhitzt.

   Nach dem Abkühlen wird mit     10o/oiger     Salzsäure ausgeschüttelt; die salzsauren Aus  züge werden mit     Kaliumkarbonat    alkalisch ge  stellt. und die ausgeschiedene Base in Äther  gesammelt. Die mit konzentrierter     Pottasche-          l.ösung    gewaschene und über     geglühter    Pott  asche getrocknete Ätherlösung wird einge  dampft und der Rückstand im Hochvakuum  destilliert, wobei der     Cyclohexyl-cyclohexyl-          methyl-carbin-@.-diäthylamino-äthyl-äther    un  ier 0,1 mm Druck bei 159-163  übergeht.  



  Zum gleichen Endprodukt gelangt man  auch, wenn man einen reaktionsfähigen Ester  des     Cyclohexyl    -     cyclohexylmethyl    -     carbinols,     z. B. ein     Halogenid,    in Gegenwart     halogen-          wasserstoffbindender    Mittel mit     ss-Diäthyl-          amino-äthanol        zur    Umsetzung bringt.



  Process for the representation of a basic ether. 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 5
EMI0001.0002
    to a compound of the formula
EMI0001.0003
    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 cyclohexyl-cy clohexylmethyl-carbin-f-diethylaminoethyl ether, boils at 159-163 ° under 0.1 mm pressure. It should find therapeutic use.



       Example: 1.3 parts of powdered sodium amide are suspended in 50 parts of absolute benzene, 6.5 parts of cyclohexylcyclohexylmethylcarbinol, obtainable from cyclohexylmethylmagnesium bromide and cyclohexylaldehyde, are added dropwise, and the mixture is stirred at 60 for 1 hour. Then 6 parts of ß-diethylamino-ethyl chloride are added and the whole is refluxed for 8 hours.

   After cooling, it is extracted with 100% hydrochloric acid; the hydrochloric extracts are made alkaline with potassium carbonate. and the precipitated base is collected in ether. The ether solution washed with concentrated potash solution and dried over calcined pot ash is evaporated and the residue is distilled in a high vacuum, the cyclohexyl-cyclohexyl-methyl-carbin - @ .- diethylamino-ethyl-ether being 0.1 mm Pressure passes at 159-163.



  The same end product is also obtained if a reactive ester of cyclohexyl-cyclohexylmethyl-carbinol, e.g. B. brings a halide, in the presence of halogenated hydrogen-binding agent with ss-diethylamino-ethanol to implement.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Äthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0034 auf eine Verbindung der Formel EMI0001.0035 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 Cyclo- hexyl-cyclohexylmethyl-carbin-,ss',diäthylamino- äthyl-äther, siedet bei 159-163 unter 0,1 mm Druck. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0034 to a compound of the formula EMI0001.0035 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 cyclohexyl-cyclohexylmethyl-carbin-, ss', diethylamino-ethyl ether, boils at 159-163 under 0.1 mm pressure.
CH269406D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269406A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269406T 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
CH269406A true CH269406A (en) 1950-06-30

Family

ID=32110434

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269406D CH269406A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269406A (en)

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