CH296525A - Process for the preparation of a bis-aminoalkoxy-alkane. - Google Patents

Process for the preparation of a bis-aminoalkoxy-alkane.

Info

Publication number
CH296525A
CH296525A CH296525DA CH296525A CH 296525 A CH296525 A CH 296525A CH 296525D A CH296525D A CH 296525DA CH 296525 A CH296525 A CH 296525A
Authority
CH
Switzerland
Prior art keywords
bis
alkane
preparation
pyrrolidino
formula
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
Publication of CH296525A publication Critical patent/CH296525A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Description

  

      Verfahren        zur    Herstellung eines     Bis-aminoalkoxy-alkans.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     Bis-amino-          alkoxy-alkans.    Das Verfahren ist dadurch ge  kennzeichnet, dass man ein     Mol    einer Verbin  dung der Formel         X,-(CII2)        io-XI       mit zwei     Mol    eines Amins der Formel  
EMI0001.0010     
    umsetzt,

   worin von den Resten     X1    und     X2     der eine Halogen und der andere einen mit  Ausnahme eines in ihm enthaltenen Sauer  stoffatoms bei der Reaktion sich abspaltenden  Rest bedeutet.  



  Die erhaltene neue Verbindung, das     1,10-          Bis-        (ss-pyrrolidino-äthoxy)        -dekan,    stellt ein  farbloses Öl vom     Siedepunkt    186 bis 192   unter 0,03 mm Druck dar. Ihr     Di-hydrobro-          mid    schmilzt bei 154 . Sie soll als Zwischen  produkt für die Herstellung von Arzneimit  teln     Verwendung    finden.

      <I>Beispiel:</I>    Zu 17,4 Teilen     1,10-Dekan-diol    und 35 Tei  len     Pyrrolidinoäthylehlorid    in 100     Volumteile          abs.        Toluol    werden. bei 50 bis 60  10,5 Teil       Natriumamid,    welches zuvor durch Mahlen in  der Kugelmühle in 50     Volumteilen        abs.        Toluol     suspendiert wurde, unter Rühren allmählich  zugegeben. Darauf wird weitere zwei Stun  den bei 50 bis 60  und anschliessend 20 Stun-    den unter Kochen am     Rückfluss    weitergerührt.

    Nach dem Erkalten wird die gebildete Base  durch Verrühren mit überschüssiger     2n-Salz-          säure    in die salzsaure Lösung übergeführt  und diese mit Äther gewaschen, mit Tierkohle  abgesaugt<B>und</B> unter Eiskühlung mit     über-          schüssiger        30        %        iger        Natronlauge        versetzt.        Die     Base wird     ausgeäthert    und, nach Trocknen  der Ätherlösung mit     Kaliumhydroxyd,    durch  fraktionierte Destillation im     Hochvakuum    ge  reinigt.

   Das so erhaltene     1,10-Bis-(fl-pyrroli-          dino-äthoxy)-dekan    ist ein farbloses Öl vom  Siedepunkt 186 bis 192  unter 0,03 mm Druck.  Das     Di-hydrobromid    schmilzt bei 154 .



      Process for the preparation of a bis-aminoalkoxy-alkane. The present patent is a process for the preparation of a bis-amino-alkoxy-alkane. The process is characterized in that one mole of a compound of the formula X, - (CII2) io-XI with two moles of an amine of the formula
EMI0001.0010
    implements,

   wherein one of the radicals X1 and X2 is halogen and the other is a radical which is split off in the reaction with the exception of an oxygen atom contained in it.



  The new compound obtained, the 1,10-bis (ss-pyrrolidino-ethoxy) decane, is a colorless oil with a boiling point of 186 to 192 under 0.03 mm pressure. Its di-hydrobromide melts at 154. It is intended to be used as an intermediate product for the manufacture of pharmaceuticals.

      <I> Example: </I> To 17.4 parts of 1,10-decanediol and 35 parts of pyrrolidinoethyl chloride in 100 parts by volume of abs. Be toluene. at 50 to 60 10.5 parts of sodium amide, which was previously obtained by grinding in a ball mill in 50 parts by volume of abs. Toluene was suspended, gradually added with stirring. The mixture is then stirred for a further two hours at 50 to 60 hours and then for 20 hours with refluxing.

    After cooling, the base formed is converted into the hydrochloric acid solution by stirring with excess 2N hydrochloric acid and this is washed with ether, suctioned off with animal charcoal and excess 30% sodium hydroxide solution is added while cooling with ice. The base is extracted with ether and, after drying the ethereal solution with potassium hydroxide, purified by fractional distillation in a high vacuum.

   The 1,10-bis- (fl-pyrrolidino-ethoxy) decane obtained in this way is a colorless oil with a boiling point of 186 to 192 under 0.03 mm pressure. The di-hydrobromide melts at 154.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Bis-amino- alkoxy-alkans, dadurch gekennzeichnet, dass man ein Mol einer Verbindung der Formel XI-(CH2) io-Xi mit zwei Mol eines Amins der Formel EMI0001.0053 umsetzt, worin von den Resten X, und X2 der eine Halogen und der andere einen mit. Ausnahme eines in ihm enthaltenen Sauer stoffatoms bei der Reaktion sich abspalten den Rest bedeutet. PATENT CLAIM Process for the preparation of a bis-amino-alkoxy-alkane, characterized in that one mole of a compound of the formula XI- (CH2) io-Xi is mixed with two moles of an amine of the formula EMI0001.0053 converts, in which of the radicals X, and X2 one halogen and the other one with. With the exception of an oxygen atom contained in it, the remainder is split off during the reaction. Die erhaltene neue Verbindung, das 1,10- Bis- (f-pyrrolidino-äthoxy) -dekan, stellt ein farbloses Öl vom Siedepunkt 186 bis 192 unter 0,03 mm Druck dar. Ihr Di-hydrobro- inid schmilzt bei 154 . UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Mol 1,1.0-Dekan- diol mit zwei Mol eines Py rrolidino-äthylhalo- genids in Gegenwart eines säurebindenden Mittels umsetzt. The new compound obtained, the 1,10-bis- (f-pyrrolidino-ethoxy) -dekan, is a colorless oil with a boiling point of 186 to 192 under 0.03 mm pressure. Your di-hydrobromide melts at 154. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that one mole of 1,1.0-decanediol is reacted with two moles of a pyrrolidino-ethyl halide in the presence of an acid-binding agent.
CH296525D 1949-12-07 1949-12-07 Process for the preparation of a bis-aminoalkoxy-alkane. CH296525A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH292802T 1949-12-07
CH296525T 1949-12-07

Publications (1)

Publication Number Publication Date
CH296525A true CH296525A (en) 1954-02-15

Family

ID=25733299

Family Applications (1)

Application Number Title Priority Date Filing Date
CH296525D CH296525A (en) 1949-12-07 1949-12-07 Process for the preparation of a bis-aminoalkoxy-alkane.

Country Status (1)

Country Link
CH (1) CH296525A (en)

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