CH269401A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269401A
CH269401A CH269401DA CH269401A CH 269401 A CH269401 A CH 269401A CH 269401D A CH269401D A CH 269401DA CH 269401 A CH269401 A CH 269401A
Authority
CH
Switzerland
Prior art keywords
ether
representation
basic ether
compound
basic
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 CH269401A publication Critical patent/CH269401A/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 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-Bu-          tyl-isobutyl-carbin-/3-diäthylamino-äthyl-äther,     siedet bei 126-132o unter 14 mm Druck. Sie  soll therapeutische Verwendung finden.  



  <I>Beispiel:</I>  Zu einer Suspension von 4 Teilen pulve  risiertem     Natriumamid    in 60 Teilen absolutem  Benzol werden 14,5 Teile     n-Butyl-isobutyl-          earbinol        zugetropft,    und 1 Stunde bei     6011     gerührt. Dann werden 13 Teile     ss-Diäthyl-          a.mino-äthylchlorid    zugegeben und das Ganze  5 Stunden unter     Rückfluss    und Rühren er-         hitzt.    Nach dem Abkühlen wird mit Wasser  versetzt und mit     10o/oiger    Salzsäure mehrmals  ausgeschüttelt.

   Die vereinigten salzsauren  Auszüge werden mit Pottasche alkalisch ge  stellt, die ausgeschiedene Base in Äther auf  genommen, die Ätherlösung mit konzentrier  ter     Pottaschelösung    gewaschen, über Natrium  sulfat getrocknet und der Äther abgedampft.  Der Rückstand siedet bei 126-132  unter  11 mm Druck. Der basische Äther ist in ver  dünnten Säuren klar löslich.  



  Zum gleichen Endprodukt gelangt man  auch, wenn man einen reaktionsfähigen Ester  des     n-Butyl-isobutyl-carbinols,    z. B. ein Halo  genid, in Gegenwart     halogenwasserstoffbin-          dender    Mittel mit     ss-Diäthylamino-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
EMI0001.0001
    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-butyl-isobutyl-carbine / 3-diethylamino-ethyl ether, boils at 126-132 ° under 14 mm pressure. It should find therapeutic use.



  <I> Example: </I> 14.5 parts of n-butyl-isobutyl-earbinol are added dropwise to a suspension of 4 parts of powdered sodium amide in 60 parts of absolute benzene, and the mixture is stirred at 6011 for 1 hour. Then 13 parts of ß-diethyl a.mino-ethyl chloride are added and the whole is heated under reflux and stirring for 5 hours. 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 ether solution is washed with concentrated potash solution, dried over sodium sulfate and the ether is evaporated. The residue boils at 126-132 under 11 mm pressure. The basic ether is clearly soluble in dilute acids.



  The same end product is also obtained if a reactive ester of n-butyl-isobutyl-carbinol, eg. B. a halide, in the presence of hydrogen halide 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 EMI0001.0020 auf eine Verbindung der Formel EMI0001.0021 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-Bu- tyl-isobutyl-carbin-ss-diäthylamino-äthyl-äther, siedet bei 126-132 unter 14 mm Druck. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0020 to a compound of the formula EMI0001.0021 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-butyl-isobutyl-carbin-ß-diethylamino-ethyl-ether, boils at 126-132 under 14 mm pressure.
CH269401D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269401A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269401T 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
CH269401A true CH269401A (en) 1950-06-30

Family

ID=32110429

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269401D CH269401A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269401A (en)

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