CH220961A - Process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine. - Google Patents

Process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine.

Info

Publication number
CH220961A
CH220961A CH220961DA CH220961A CH 220961 A CH220961 A CH 220961A CH 220961D A CH220961D A CH 220961DA CH 220961 A CH220961 A CH 220961A
Authority
CH
Switzerland
Prior art keywords
propyl
isobutylpyrrolidine
dioxo
preparation
ammonia
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH220961A publication Critical patent/CH220961A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung     -von        2,4-Dioao-3-n-propyl-3-isobutylpyrrolidin.       Nach dem Verfahren des     Hauptpatentes     wird     2,4-Dioxo-3,3-di-n-propylpyrrolidin    da  durch gewonnen, dass auf     a;a-Di=n-propyl-y-          halogenacetessigester    in Anwesenheit eines       Lösungsmittels    Ammoniak einwirken gelas  sen wird.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     2,4-Dioxo-          3-n-propyl-3-isobutylpyrrolidin,    welches da  durch gekennzeichnet ist, dass auf     a-n-Pro-          pyl-a-isobutyl-y-halogenacetessigester    in. An  wesenheit eines     Lösungsmittels    Ammoniak  einwirken gelassen wird.  



  Das bisher unbekannte     2,4-Dioxo-3-n-pro-          pyl-3-isobutylpyrrolidin    schmilzt bei 101 bis  102'. Es siedet unter 12 mm Druck bei 180  bis<B>183</B>  . In Wasser ist es ziemlich schwer  löslich, leicht in den üblichen organischen  Lösungsmitteln. Da es Schlafwirkung besitzt,  soll es- als Arzneimittel verwendet werden.  <I>Beispiel:</I>  Eine eiskalte     Lösung    von 70 Teilen Am  moniakgas und 307 Teilen a-n-Propyl-a-iso-         butyl-y-brom-acetessigester        in    350     Teilen    Al  kohol wird während 12     Stunden    stehen ge  lassen.

   Die Umsetzung, die an dem     Ausfallen     des     Ammoniumbromids    verfolgt werden kann,       wird    dadurch vervollständigt, dass man  6     Stunden    auf 50 bis 60   erwärmt. Die  vom     Ammoniumbromid        getrennte    Lösung  wird im Vakuum eingeengt. Der Rückstand  wird mit dreifach normaler     Natrönlauge    bis  zur deutlich     phenolphthaleinalkalischen    Re  aktion versetzt. Das abgeschiedene 01     wird     in Benzol     aufgenommen    und nach dem Ver  jagen des Benzols im     Vakuum    destilliert.

   Das  Destillat wird aus     Dibutyläther        umkristalli-          siert.  



  Process for the preparation of 2,4-Dioao-3-n-propyl-3-isobutylpyrrolidine. According to the process of the main patent, 2,4-dioxo-3,3-di-n-propylpyrrolidine is obtained by allowing ammonia to act on a; a-di = n-propyl-y-haloacetoacetic ester in the presence of a solvent.



  The present patent relates to a process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine, which is characterized in that an-propyl-α-isobutyl-γ-haloacetoacetic ester in. An the presence of a solvent ammonia is allowed to act.



  The previously unknown 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine melts at 101 to 102 '. It boils at 180 to <B> 183 </B> under 12 mm pressure. It is rather sparingly soluble in water, easily soluble in common organic solvents. Since it has sleep effects, it should be used as a medicine. <I> Example: </I> An ice-cold solution of 70 parts of ammonia gas and 307 parts of a-n-propyl-a-isobutyl-y-bromo-acetic acid ester in 350 parts of alcohol is left to stand for 12 hours.

   The reaction, which can be followed by the precipitation of the ammonium bromide, is completed by heating to 50 to 60 hours. The solution separated from the ammonium bromide is concentrated in vacuo. Triple normal sodium hydroxide solution is added to the residue until the reaction is clearly phenolphthalein-alkaline. The precipitated oil is taken up in benzene and, after the benzene has been removed, distilled in vacuo.

   The distillate is recrystallized from dibutyl ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 2,4-Dioxo- 3-n-propyl-3-isobutylpyrrolidin, dadurch ge kennzeichnet, dass auf a-n-Propyl-a-isobutyl- y-halogenacetessigester in Anwesenheit eines Lösungsmittels Ammoniak einwirken gelas sen wird. Das bisher unbekannte 2,4-Dioxo-3-n-pro- pyl-3-isobutylpyrrolidin schmilzt bei 101 bis 102 . PATENT CLAIM: Process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine, characterized in that ammonia is allowed to act on a-n-propyl-a-isobutyl-y-haloacetoacetic ester in the presence of a solvent. The previously unknown 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine melts at 101 to 102. Es siedet unter 12 mm Druck bei 180 bis 183 . In Wasser ist es ziemlich. schwer löslich, leicht in den üblichen organi- sehen Lösungsmitteln. Da es Sehlafwirkung besitzt, soll es als Arzneimittel verwendet werden. It boils at 180 to 183 under 12 mm pressure. It's pretty in water. poorly soluble, easily see in the usual organic solvents. Since it has visual sleep effects, it should be used as a medicine.
CH220961D 1938-11-30 1939-10-13 Process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine. CH220961A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE220961X 1938-11-30
CH213347T 1939-10-13

Publications (1)

Publication Number Publication Date
CH220961A true CH220961A (en) 1942-04-30

Family

ID=25725410

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220961D CH220961A (en) 1938-11-30 1939-10-13 Process for the preparation of 2,4-dioxo-3-n-propyl-3-isobutylpyrrolidine.

Country Status (1)

Country Link
CH (1) CH220961A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2727897A (en) * 1952-02-08 1955-12-20 Ciba Pharm Prod Inc Dioxo-pyrrolidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2727897A (en) * 1952-02-08 1955-12-20 Ciba Pharm Prod Inc Dioxo-pyrrolidines

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