CH269407A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269407A
CH269407A CH269407DA CH269407A CH 269407 A CH269407 A CH 269407A CH 269407D A CH269407D A CH 269407DA CH 269407 A CH269407 A CH 269407A
Authority
CH
Switzerland
Prior art keywords
ether
representation
basic ether
compound
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 CH269407A publication Critical patent/CH269407A/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

Landscapes

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

Description

  

  Verfahren zur Darstellung eines basischen Äthers.    Gegenstand vorliegenden Patentes ist ein  Verfahren zur Darstellung eines basischen       Äthers.    Das Verfahren ist dadurch     gel@enn-          zeiehnet,        dass    man eine Verbindung der Formel  
EMI0001.0005     
    auf eine Verbindung der Formel  
EMI0001.0006     
    worin N und Y zwei     reaktionsfäbige,    mit Aus  nahme eines in einem von ihnen enthaltenen  Sauerstoffatoms, sieh bei der Reaktion abspal  tende Reste bedeuten,     einwirken    lässt.  



  Die erhaltene neue     Verbindung,    der     n-Bu-          tyl    -     isobutyl    -     carbin.-P-dimetliylamino-ä.thyl-          äther,    siedet bei     8r90     unter 12 mm Druck.  Sie soll     therapeutische    Verwendung finden.  



  <I>Beispiel:</I>  Zu einer Suspension von 4 Teilen pulveri  sierten)     Natriumamid    in 60 Teilen absolutem  Benzol werden 14,4 Teile     n-Butyl-isobuty        1-          earbinol        zugetropft    und eine Stunde bei<B>60'</B>  gerührt. Dann werden 10,8 Teile     f'-Dimethyl-          airiino-ätliyletilorid    zugegeben     und        das        (Tanze          :i        Stunden    unter     Riickfluss    und Rühren er  hitzt.

   Nach dein Abkühlen wird mit Wasser  versetzt und mit     l0o/oiger    Salzsäure mehrmals  ausgeschüttelt. Die vereinigten salzsauren Aus  züge werden mit Pottasche alkalisch gestellt,    die ausgeschiedene Base in Äther aufgenom  men, die Ätherlösung mit konzentrierter     Pott-          asehelösung    gewaschen, über Natriumsulfat  getrocknet und der Äther abgedampft. Der als  Rückstand erhaltene basische Äther siedet bei       82-90o    unter 12 mm Druck.  



  Zum gleichen. Endprodukt gelangt.     man     auch, wenn man einen reaktionsfähigen Ester  des     n-Butyl-isobutyl-carbinols,    z. B. ein Halo  genid, in Gegenwart säurebindender Mittel  mit     l-Dimethylamino-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
EMI0001.0005
    to a compound of the formula
EMI0001.0006
    wherein N and Y two reactive, with the exception of one oxygen atom contained in one of them, see mean residues splitting off during the reaction, can act.



  The new compound obtained, the n-butyl-isobutyl-carbin.-P-dimethylamino-ethyl-ether, boils at 890 under 12 mm pressure. It should find therapeutic use.



  <I> Example: </I> 14.4 parts of n-butyl-isobutyl-1-earbinol are added dropwise to a suspension of 4 parts of pulverized sodium amide in 60 parts of absolute benzene, and the mixture is heated to 60% for one hour > stirred. Then 10.8 parts of f'-dimethylairiino-ätliyletilorid are added and the (dance: i hours under reflux and stirring he is heated.

   After cooling, water is added and the mixture is extracted several times with 10% hydrochloric acid. The combined hydrochloric acid extracts are made alkaline with potash, the precipitated base is taken up in ether, the ethereal solution is washed with concentrated potash solution, dried over sodium sulphate and the ether is evaporated. The basic ether obtained as residue boils at 82-90 ° under 12 mm pressure.



  At the same time. End product arrives. you also, if you have a reactive ester of n-butyl-isobutyl-carbinol, z. B. a halo genide, in the presence of acid-binding agents with l-dimethylamino-ethanol to implement.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Äthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0038 auf eine Verbindung der Formel EMI0001.0039 worin X und Y zwei reaktionsfähige, mit Aus nahme eines in einem von ihnen enthaltenen Sauerstoffatoms, sieh bei der Reaktion abspal tende Reste bedeuten, einwirken lässt. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0038 to a compound of the formula EMI0001.0039 where X and Y two reactive, with the exception of one oxygen atom contained in one of them, see mean residues splitting off during the reaction, can act. Die erhaltene neue Verbindung, der n-Bii- tyl - isobuty 1. - earbin <I>.</I> f3 <I>-</I> dimethylamino- äthyl- ätlier, siedet bei 8''-90o unter 12 mm Druck. The new compound obtained, the n-biityl - isobuty 1. - earbin <I>. </I> f3 <I> - </I> dimethylamino-ethyl-eter, boils at 8``-90o below 12 mm Pressure.
CH269407D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269407A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269407T 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
CH269407A true CH269407A (en) 1950-06-30

Family

ID=32110435

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269407D CH269407A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269407A (en)

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