CH269403A - Process for the representation of a basic ether. - Google Patents

Process for the representation of a basic ether.

Info

Publication number
CH269403A
CH269403A CH269403DA CH269403A CH 269403 A CH269403 A CH 269403A CH 269403D A CH269403D A CH 269403DA CH 269403 A CH269403 A CH 269403A
Authority
CH
Switzerland
Prior art keywords
ether
representation
compound
diethylamino
propyl
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 CH269403A publication Critical patent/CH269403A/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)

Description

  

  Verfahren zur Darstellung eines basischen Äthers.    Gegenstand vorliegenden Patentes ist ein  Verfahren zur Darstellung eines basischen  Äthers. Das Verfahren ist dadurch gekenn  zeichnet;     class    man eine Verbindung der  Formel  
EMI0001.0002     
    auf eine Verbindung der Formel  
EMI0001.0003     
    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-Pro-          pyl    -     cyclopentyl    -     carbin-ss-diäthylamino-äthyl-          äther,    siedet bei 129-137  unter 12 mm     Druck.     Sie soll therapeutische Verwendung finden.       Beispiel:     Man suspendiert. 2 Teile pulverisiertes       Natriumamid    in 50 Teilen absolutem Benzol,  tropft 7,1 Teile     n-Propyl-cyclopentyl-carbinol     zu und rührt 1 Stunde bei 60o. Dann werden  8 Teile     ss-Diäthylamino-ätliylchlorid    zugefügt  und das Ganze 8 Stunden unter Rückfloss  erhitzt.

   Nach dem Abkühlen wird mit     10o/oiger     Salzsäure     ausgesehüttelt;    die salzsauren Aus  züge werden mit     Kaliumearbonat    alkalisch  gestellt und die ausgeschiedene Base in Äther  gesammelt. Die mit konzentrierter Pottasehe-         lösung    gewaschene und über geglühter Pott  asche getrocknete Ätherlösung wird einge  dampft und der Rückstand im Vakuum destil  liert, wobei der     n-Propyl-cyclopentyl-carbin-          ss-diäthylamino-äthyl-äther    unter 12 mm Druck  bei 129-137o übergeht.  



  Zum gleichen Endprodukt gelangt man  auch, wenn man einen reaktionsfähigen Ester  des     n-Propyl-cy        clopentyl-carbinols,    z. B. ein       Halogenid,    in Gegenwart     halogenwasserstoff-          bindender    Mittel mit     P-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 method is characterized by this; class a compound of the formula
EMI0001.0002
    to a compound of the formula
EMI0001.0003
    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-propyl-cyclopentyl-carbin-ß-diethylamino-ethyl ether, boils at 129-137 under 12 mm pressure. It should find therapeutic use. Example: You are suspended. 2 parts of powdered sodium amide in 50 parts of absolute benzene, 7.1 parts of n-propyl-cyclopentyl-carbinol are added dropwise and the mixture is stirred at 60 ° for 1 hour. Then 8 parts of ß-diethylamino-ätliylchlorid are added and the whole is heated under reflux for 8 hours.

   After cooling, it is shaken out with 10% hydrochloric acid; the hydrochloric acid extracts are made alkaline with potassium carbonate and the precipitated base is collected in ether. The ether solution, washed with concentrated potash solution and dried over calcined pot ash, is evaporated and the residue is distilled in vacuo, the n-propyl-cyclopentyl-carbine-diethylamino-ethyl-ether under 12 mm pressure at 129-137o transforms.



  The same end product is also obtained if you use a reactive ester of n-propyl-cy clopentyl-carbinol, e.g. B. a halide, in the presence of hydrogen halide binding agents with P-diethylamino-ethanol to implement.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Äthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0026 auf eine Verbindung der Formel EMI0001.0027 worin X und Y zwei reaktionsfähige, rnit 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-Pro- pyl - cy clopentyl-.carbin-ss-diäthylamino-äthy 1- äther, siedet bei 129-137 unter 12 mm Druck. PATENT CLAIM: Process for the preparation of a basic ether, characterized in that a compound of the formula EMI0001.0026 to a compound of the formula EMI0001.0027 where X and Y are two reactive radicals which, with the exception of one oxygen atom contained in one of them, are radicals that split off during the reaction. The new compound obtained, the n-propyl-cyclopentyl-carbine-ss-diethylamino-ethy 1 -ether, boils at 129-137 under 12 mm pressure.
CH269403D 1942-09-23 1943-08-11 Process for the representation of a basic ether. CH269403A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2397799X 1942-09-23
CH269403T 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
CH269403A true CH269403A (en) 1950-06-30

Family

ID=32110431

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269403D CH269403A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.

Country Status (1)

Country Link
CH (1) CH269403A (en)

Similar Documents

Publication Publication Date Title
CH269403A (en) Process for the representation of a basic ether.
CH269405A (en) Process for the representation of a basic ether.
CH269406A (en) Process for the representation of a basic ether.
CH269401A (en) Process for the representation of a basic ether.
CH269404A (en) Process for the representation of a basic ether.
CH269413A (en) Process for the representation of a basic ether.
CH269409A (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.
CH269408A (en) Process for the representation of a basic ether.
CH269402A (en) Process for the representation of a basic ether.
CH269411A (en) Process for the representation of a basic ether.
CH269407A (en) Process for the representation of a basic ether.
CH281966A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH243020A (en) Process for the preparation of a basic ester.
CH255628A (en) Process for the preparation of an aromatic acylsulfonamide.
CH243024A (en) Process for the preparation of a basic ester.
CH243022A (en) Process for the preparation of a basic ester.
CH296527A (en) Process for the preparation of a bis-aminoalkoxy-alkane.
CH255627A (en) Process for the preparation of an aromatic acylsulfonamide.
CH281947A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH249050A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH243014A (en) Process for the preparation of an acylated, aliphatic aminocarboxamide.
CH281949A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH268458A (en) Process for the preparation of a basic ester.