CH240143A - Process for the preparation of a basic aralkyl ether. - Google Patents

Process for the preparation of a basic aralkyl ether.

Info

Publication number
CH240143A
CH240143A CH240143DA CH240143A CH 240143 A CH240143 A CH 240143A CH 240143D A CH240143D A CH 240143DA CH 240143 A CH240143 A CH 240143A
Authority
CH
Switzerland
Prior art keywords
basic
ether
preparation
aralkyl ether
parts
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 CH240143A publication Critical patent/CH240143A/en

Links

Classifications

    • 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
    • C07C217/10—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 to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
    • 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
    • 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)

Description

  

  Verfahren zur Darstellung eines basischen     Aralkyläthers.            Gegenstand    des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Darstellung eines  basischen     Aralkyläthers    aus     Cyclohegyl-(o-          methoxy-phenyl)-carbinol    und     Diäthylamino-          äthanol.    Das Verfahren ist dadurch gekenn  zeichnet, dass ein reaktionsfähiger Ester des  einen Alkohols mit einem     Alkoholat    des       andern.    Alkohols umgesetzt wird.

   Der erhal  tene     Cyclo#hexyl    -     (o-methogy-phenyl)    -     carbin-          (diäthylaminoäthyl)-äther    ist eine Flüssigkeit  vom     Kp.        a,,    161-163 ; er soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  Zu einer Suspension von 4 Teilen pulveri  siertem     Natriumamid        in    200 Teilen absolu  tem Benzol werden 22 Teile     Cyclohexyl-          (o-methoxy-phenyl)-carbinol        zugetropft    und  eine Stunde bei 60      gerührt.    Dann werden  14 Teile     ss-Chloräthyl-diäthylamin    zugegeben  und das Ganze sechs Stunden unter     Rückfluss     und Rühren erhitzt. Nach dem Abkühlen wird  mit. Wasser versetzt und mit     10%iger    Salz  säure mehrmals ausgeschüttelt.

   Die vereinig-         ten        sälzsauren    Auszüge werden mit Pottasche  alkalisch gemacht, die ausgeschiedene     Base        in     Äther aufgenommen, die     Atherlösung    mit  konzentrierter     Pottaschelösung    gewaschen,  über fester Pottasche getrocknet und der  Äther abgedampft. Der Rückstand siedet  unter 0,9     mm    bei 161-163 .  



  Dieselbe Verbindung kann auch auf fol  gende Weise erhalten werden: In einer Lö  sung von 11 Teilen     Diäthylaminoäthanol        in     40     Teilen    Benzol werden 2 Teile Natrium auf  gelöst. Nach .dem Erkalten wird die berech  nete Menge     Cyclohexyl-(o-methoxy-phenyl)-          carbinyl-chlorid    in     Portionen    zugegeben. Nach  Abklingen der Reaktion wird noch eine Stunde  lang am     Rückflusskühler    auf dem Wasserbad  erhitzt, alsdann gekühlt, mit Wasser aus  geschüttelt     und    schliesslich unter Kühlung mit       verdünnter    Salzsäure verrührt.

   Nach noch  maligem     Waschen    des Benzols mit Wasser  werden die vereinigten Auszüge     mit        Pottasche     gefällt und die ausgeschiedene Base in Äther  aufgenommen. Nach Entfernen des Lösungs  mittels destilliert die Base bei l61-163  und      0,9 mm. Der neue Äther soll therapeutische       Verwendung    finden.



  Process for the preparation of a basic aralkyl ether. The subject of the present Zusatzpaten tes is a method for the preparation of a basic aralkyl ether from cyclohegyl- (o-methoxy-phenyl) -carbinol and diethylamino-ethanol. The method is characterized in that a reactive ester of one alcohol with an alcoholate of the other. Alcohol is implemented.

   The obtained cyclo # hexyl - (o-methogy-phenyl) -carbine- (diethylaminoethyl) -ether is a liquid of Kp. A ,, 161-163; it should find therapeutic use.



  <I> Example: </I> 22 parts of cyclohexyl (o-methoxyphenyl) carbinol are added dropwise to a suspension of 4 parts of powdered sodium amide in 200 parts of absolute benzene, and the mixture is stirred at 60 for one hour. 14 parts of ß-chloroethyl-diethylamine are then added and the whole is heated under reflux and stirring for six hours. After cooling down, use. Added water and extracted several times with 10% hydrochloric acid.

   The combined hydrochloric acid extracts are made alkaline with potash, the base which has separated out is taken up in ether, the ether solution is washed with concentrated potash solution, dried over solid potash and the ether is evaporated. The residue boils below 0.9 mm at 161-163.



  The same compound can also be obtained in the following manner: 2 parts of sodium are dissolved in a solution of 11 parts of diethylaminoethanol in 40 parts of benzene. After cooling down, the calculated amount of cyclohexyl (o-methoxyphenyl) carbinyl chloride is added in portions. After the reaction has subsided, the mixture is heated in the reflux condenser on the water bath for a further hour, then cooled, shaken out with water and finally stirred with dilute hydrochloric acid while cooling.

   After washing the benzene again with water, the combined extracts are precipitated with potash and the base which has separated out is taken up in ether. After removing the solution by means of the base distilled at 161-163 and 0.9 mm. The new ether should be used therapeutically.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Aralkyläthers aus Cyclohexyl-(o-methoxy- phenyl)-ca.rbinol und Diäthylaminoäthanol, dadurch gekennzeichnet, dass ein reaktions- fähiger Ester des einen Alkohols mit einem Alkoholat des andern Alkohols umgesetzt wird. Der erhaltene Cyclohexyl-(o-methoxy- phenyl)-c@a.rbin-(diäthylaminoäthyl)-äther ist eine Flüssigkeit vom Kp.o" 161-163 ; er soll therapeutische Verwendung finden. Claim: Process for the preparation of a basic aralkyl ether from cyclohexyl- (o-methoxyphenyl) -ca.rbinol and diethylaminoethanol, characterized in that a reactive ester of one alcohol is reacted with an alcoholate of the other alcohol. The cyclohexyl- (o-methoxyphenyl) -c@a.rbin- (diethylaminoethyl) -ether obtained is a liquid of bp 161-163; it is said to be used in therapy.
CH240143D 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether. CH240143A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH240143T 1942-09-23
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
CH240143A true CH240143A (en) 1945-11-30

Family

ID=32110427

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240143D CH240143A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.

Country Status (1)

Country Link
CH (1) CH240143A (en)

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