CH269408A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269408A
CH269408A CH269408DA CH269408A CH 269408 A CH269408 A CH 269408A CH 269408D A CH269408D A CH 269408DA CH 269408 A CH269408 A CH 269408A
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 CH269408A publication Critical patent/CH269408A/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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring 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)
  • 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, sieh bei der Reaktion abspal  tende Reste bedeuten, einwirken lässt.  



  Die erhaltene neue Verbindung, der     Iso-          butyl    -     cyclopentyl    -     carbin,-fi-        dimethylamino        -          äthyl-äther,    siedet bei 123-130o unter 12 mm  Druck. Sie soll therapeutische Verwendung  finden.  



  <I>Beispiel:</I>  Zu einer Suspension von 4 Teilen pulveri  siertem     Natriumamid    in 60 Teilen absolutem  Benzol werden 15,6 Teile     Isobutyl-cyclopentyl-          carbinol        zugetropft    und 1 Stunde bei<B>601</B>  gerührt. Dann werden 10,8 Teile     fl'-Dimethyl-          amino-ätliylehlorid    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    Aus  züge werden mit Pottasche alkalisch gestellt,  die ausgeschiedene Base in Äther aufgenom  men, die Ätherlösung mit konzentrierter Pott  aschelösung gewaschen, über Natriumsulfat  getrocknet und der Äther abgedampft. Der  als Rückstand erhaltene basische Äther siedet  bei 123-130o unter 12 mm Druck.  



  Zum gleichen     Endprodukt    gelangt man  auch, wenn man einen reaktionsfähigen Ester  des     Isobutyl-cyclopentyl-carbinols,    z. B. ein       Halogenid,    in Gegenwart säurebindender Mit  tel mit     ss-Dimethylamino-äthanol    zur Umset  zung bringt.



  Process for the representation of a basic ether. Subject of the present patent is. a method for the representation 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
    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.



  The new compound obtained, the isobutyl-cyclopentyl-carbin, -fi- dimethylamino-ethyl-ether, boils at 123-130 ° under 12 mm pressure. It should find therapeutic use.



  <I> Example: </I> 15.6 parts of isobutyl-cyclopentyl-carbinol 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 <B> 601 </B> for 1 hour. Then 10.8 parts of fl'-dimethylamino-ethyl chloride are added and the whole is heated under reflux and stirring for 5 hours. After cooling down, use. 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 sulfate and the ether is evaporated. The basic ether obtained as residue boils at 123-130o under 12 mm pressure.



  The same end product is also obtained if a reactive ester of isobutyl-cyclopentyl-carbinol, eg. B. a halide, in the presence of acid-binding agents with ss-dimethylamino-ethanol for implementation.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Äthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0025 auf eine Verbindung der Formel EMI0001.0026 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 Iso- buty 1- cyclopentyl - carbin,-ss - dimethylamino - äthyl-äther, siedet bei<B>123-1300</B> unter 12 mm Druck. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0025 to a compound of the formula EMI0001.0026 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, isobuty 1-cyclopentyl-carbine, -ss-dimethylamino-ethyl-ether, boils at 123-1300 under 12 mm pressure.
CH269408D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269408A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269408T 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
CH269408A true CH269408A (en) 1950-06-30

Family

ID=32110436

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269408D CH269408A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269408A (en)

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