CH240135A - Process for the preparation of a basic aralkyl ether. - Google Patents

Process for the preparation of a basic aralkyl ether.

Info

Publication number
CH240135A
CH240135A CH240135DA CH240135A CH 240135 A CH240135 A CH 240135A CH 240135D A CH240135D A CH 240135DA CH 240135 A CH240135 A CH 240135A
Authority
CH
Switzerland
Prior art keywords
basic
preparation
ether
parts
aralkyl 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 CH240135A publication Critical patent/CH240135A/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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines basischen     Aralkyläthers.       Gegenstand des     vorliegenden    Zusatzpaten  tes ist ein Verfahren zur Darstellung eines  basischen     Aralkyläthers    aus     a-Cyclohexyl-          benzylalkohol    und     Diäthylaminoäthanol.    Das  Verfahren ist dadurch gekennzeichnet, dass  ein reaktionsfähiger Ester des einen Alkohols  mit einem     Alkoholat    des andern Alkohols  umgesetzt wird.

   Der erhaltene     a-Cyclohexyl-          benzyl    -     (diäthylaminoäthyl)    -     äther    ist eine  Flüssigkeit vom     gp.        ",ss        130-132 ;    er soll       therapeutische    Verwendung finden.  



  <I>Beispiel:</I>  Zu einer Suspension von 20 Teilen pulveri  siertem     Natriumamid    in 300 Teilen     absol.     Benzol werden 95 Teile     Cyclohexyl-phenyl-          carbinol        zugetropft    und 1 Stunde bei 60  ge  rührt. Dann werden 70 Teile     ss-Chloräthyl-          diäthylamin    zugegeben und das Ganze 6 Stun  den unter     Rückfluss    und Rühren erhitzt. Nach  dem Abkühlen wird mit Wasser versetzt und  mit 10%iger Salzsäure mehrmals aus  geschüttelt.

   Die vereinigten salzsauren Aus-         züge    werden mit Pottasche alkalisch gemacht,  die ausgeschiedene Base     in    Äther aufgenom  men, die Ätherlösung mit     konz.    Pottasche  lösung gewaschen, über fester Pottasche ge  trocknet und der Äther abgedampft. Der  Rückstand siedet bei 0,6 mm bei     130-1ä2 .     Ausbeute 95 Teile.  



  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     a-Cyclohexyl-benzylchlorid    in  Portionen zugegeben. Nach Abklingen der  Reaktion wird noch eine Stunde lang am       Rückflusskühler    auf dem Wasserbad erhitzt,  alsdann gekühlt, mit Wasser ausgeschüttelt  und schliesslich unter Kühlung mit verdünn  ter Salzsäure verrührt. Nach nochmaligem  Waschen des Benzols mit Wasser werden die  vereinigten Auszüge mit Pottasche gefällt  und die abgeschiedene Base in Äther auf  genommen. Nach Entfernen des Lösungs-      mittels destilliert die Base bei     130-13?'    und  0,6 mm.

   Der neue Äther soll     therapeutisehe     Verwendung finden.



  Process for the preparation of a basic aralkyl ether. Subject of the present Zusatzpaten tes is a method for the preparation of a basic aralkyl ether from α-cyclohexyl benzyl alcohol and diethylaminoethanol. The method is characterized in that a reactive ester of one alcohol is reacted with an alcoholate of the other alcohol.

   The obtained a-cyclohexylbenzyl - (diethylaminoethyl) - ether is a liquid of gp. ", pp. 130-132; it should find therapeutic use.



  <I> Example: </I> To a suspension of 20 parts of powdered sodium amide in 300 parts of absol. Benzene, 95 parts of cyclohexyl-phenyl-carbinol are added dropwise and the mixture is stirred at 60 for 1 hour. Then 70 parts of β-chloroethyl diethylamine are added and the whole thing is heated under reflux and stirring for 6 hours. After cooling, water is added and the mixture is shaken out 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 with conc. Washed potash solution, dried over solid potash and evaporated the ether. The residue boils at 0.6 mm at 130-1-2. Yield 95 parts.



  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, the calculated amount of α-cyclohexylbenzyl 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, extracted 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 solvent, the base distills at 130-13? ' and 0.6 mm.

   The new ether should be used in therapy.

Claims (1)

PATENANSPRUCH: Verfahren zur Darstellung eines basischen Aralkylätbers aus a-Cyclohexyl-benzylall:o- hol und Diäthylaminoäthanol, dadurch ge- kennzeichnet, da.ss ein reaktionsfähiger Ester des einen Alkohols znit einem Alkoholat des andern Alkohols umgesetzt wird. Claim to the patent: Process for the preparation of a basic aralkyl ether from α-cyclohexylbenzylall: o-hol and diethylaminoethanol, characterized in that a reactive ester of one alcohol is reacted with an alcoholate of the other alcohol. Der er haltene a-Cyclohexyl-benzyl-(diäthylamino- ä.thyl)-äther ist eine Flüssigkeit vom Kp. ,E 130-1.32 ; er soll therapeutische Verwendung finden. He obtained a-cyclohexyl-benzyl (diethylamino ä.thyl) ether is a liquid of bp., E 130-1.32; it should find therapeutic use.
CH240135D 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether. CH240135A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH240135T 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
CH240135A true CH240135A (en) 1945-11-30

Family

ID=32110426

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240135D CH240135A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.

Country Status (1)

Country Link
CH (1) CH240135A (en)

Similar Documents

Publication Publication Date Title
CH240135A (en) Process for the preparation of a basic aralkyl ether.
CH240143A (en) Process for the preparation of a basic aralkyl ether.
CH240133A (en) Process for the preparation of a basic aralkyl ether.
CH149007A (en) Process for the preparation of a halogen-containing basic ether.
AT126160B (en) Process for the preparation of aminoketo alcohols.
AT159960B (en) Process for the preparation of aminobenzenesulfonic acid amide compounds.
AT92407B (en) Process for the preparation of 1-allyl-3,7-dimethylxanthine.
CH269411A (en) Process for the representation of a basic ether.
CH242287A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH269402A (en) Process for the representation of a basic ether.
CH269409A (en) Process for the representation of a basic ether.
CH242245A (en) Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240379A (en) Process for the preparation of an acylated, aliphatic aminocarboxamide.
CH269407A (en) Process for the representation of a basic ether.
CH269408A (en) Process for the representation of a basic ether.
CH269410A (en) Process for the representation of a basic ether.
CH269412A (en) Process for the representation of a basic ether.
CH199676A (en) Process for the preparation of a substituted thiazolecarboxamide.
CH269401A (en) Process for the representation of a basic ether.
CH240376A (en) Process for the preparation of an acylated, aliphatic aminocarboxamide.
CH249050A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240389A (en) Process for the preparation of an acylated, aliphatic aminocarboxamide.
CH217133A (en) Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative.
CH242288A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH240392A (en) Process for the preparation of an acylated, aliphatic aminocarboxamide.