CH220960A - Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine. - Google Patents

Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine.

Info

Publication number
CH220960A
CH220960A CH220960DA CH220960A CH 220960 A CH220960 A CH 220960A CH 220960D A CH220960D A CH 220960DA CH 220960 A CH220960 A CH 220960A
Authority
CH
Switzerland
Prior art keywords
dioxo
preparation
diethylpyrrolidine
ammonia
diethyl
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 CH220960A publication Critical patent/CH220960A/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-Dioxo-3,3-cliätliylpyrrolidin.       Nach dem Verfahren des Hauptpatentes  wird     2,4-Dioxo-3,3-di-n-propyl-pyrrolidin    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-          3,3-diäthyl-pyrrolidin,    welches dadurch ge  kennzeichnet ist, dass auf     a,a-Diäthyl-y-halo-          genacetessigester    in Anwesenheit eines Lö  sungsmittels     Ammoniak        einwirken    gelassen  wird.  



  Das bisher unbekannte     2,4-Dioxo-3,3-di-          äthyl-pyrrolidin    bildet farblose Kristalle, die  bei 88 bis 89   schmelzen. Es siedet bei 12 mm  Druck     zwischen    175 bis<B>1-78.'</B> und ist in  Wasser, sowie in den üblichen organischen  Lösungsmitteln leicht löslich.     Da--es    Schlaf  wirkung besitzt, soll es als     Arzneimittel    ver  wendet werden.  



  <I>Beispiel:</I>  Man leitet unter guter Kühlung in 350  Teile Alkohol 70 Teile     Ammoniakgas    ein. Zu    dem noch kalten, alkoholischen Ammoniak  gibt man auf einmal 265 Teile     a,a-Diäthyl-          y-brom-acetessigester.    Nach einiger Zeit er  wärmt sich die Lösung ganz langsam und  bald beginnt die     Ausscheidung    von     Ammo-          niumbromid.    Nach 24 Stunden werden das  überschüssige     Ammoniakgäs    und der Alkohol  im Vakuum     abdestilliert.    - Der Rückstand  wird zweimal mit 200 Teilen     Benzol-Alkohol-          Gemisch    (1 :

   1) ausgekocht und das ungelöste       Ammoniumbromid        abgetrennt.    Der nach  dem Vertreiben des Lösungsmittels verblei  bende ölige     Rückstand.wird    im Vakuum de  stilliert. Das sofort fest werdende Destillat  wird in der doppelten Menge Benzol warm  gelöst und die Lösung bis zur Trübung mit       Petroläther    versetzt, worauf sich Kristalle  ausscheiden.



  Process for the preparation of 2,4-dioxo-3,3-cliätliylpyrrolidin. According to the process of the main patent, 2,4-dioxo-3,3-di-n-propyl-pyrrolidine is obtained by the fact that a, a-di-n-propyl-y-haloacetoacetic ester in the presence of a solvent ammonia act sen becomes.



  The subject of the present patent is a process for the preparation of 2,4-dioxo-3,3-diethyl-pyrrolidine, which is characterized in that a, a-diethyl-y-haloacetoacetic ester acts in the presence of a solvent, ammonia is left.



  The previously unknown 2,4-dioxo-3,3-diethylpyrrolidine forms colorless crystals that melt at 88 to 89. At 12 mm pressure it boils between 175 to <B> 1-78. '</B> and is easily soluble in water as well as in common organic solvents. Since it has a sleep effect, it should be used as a medicine.



  <I> Example: </I> 70 parts of ammonia gas are introduced into 350 parts of alcohol with good cooling. 265 parts of α, α-diethyl-γ-bromo-acetoacetic ester are added all at once to the still cold, alcoholic ammonia. After a while the solution warms up very slowly and soon the ammonium bromide begins to excrete. After 24 hours, the excess ammonia and the alcohol are distilled off in vacuo. - The residue is washed twice with 200 parts of a benzene-alcohol mixture (1:

   1) boiled and the undissolved ammonium bromide separated. The oily residue remaining after the solvent has been driven off is distilled in vacuo. The distillate, which solidifies immediately, is dissolved in double the amount of warm benzene and petroleum ether is added to the solution until it becomes cloudy, whereupon crystals separate out.

Claims (1)

.PATENTANSPRUCH: Verfahren zur Darstellung von 2,4-Dioxo- 3,3-diäthyl-pyrrolidin, dadurch gekennzeich net, dass auf a,a-Diäth-#Tl-y-halogenacetessig- ester in Anwesenheit eines Lösungsmittels Ammoniak einwirken gelassen wird. Das bisher unbekannte 2,4-Diogo-3,3-di- äthyl-pyrrolidin bildet farblose Kristalle, die bei 88 bis 89 schmelzen. .PATENT CLAIM: Process for the preparation of 2,4-dioxo- 3,3-diethyl-pyrrolidine, characterized in that ammonia is allowed to act on a, a-dieth- # Tl-y-haloacetoacetic ester in the presence of a solvent. The previously unknown 2,4-diogo-3,3-diethylpyrrolidine forms colorless crystals that melt at 88 to 89. Es siedet bei 12 mm Druck zwischen I75 bis<B>178</B> und ist in Was ser, sowie in den üblichen organischen Lö- sungsmitteln leicht löslich. Da es Schlafwir- kung besitzt, soll es als Arzneimittel verwen det werden. At a pressure of 12 mm, it boils between 175 and 178 and is easily soluble in water as well as in the usual organic solvents. Since it has a sleep effect, it should be used as a medicine.
CH220960D 1938-11-30 1939-10-13 Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine. CH220960A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE220960X 1938-11-30
CH213347T 1939-10-13

Publications (1)

Publication Number Publication Date
CH220960A true CH220960A (en) 1942-04-30

Family

ID=25725409

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220960D CH220960A (en) 1938-11-30 1939-10-13 Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine.

Country Status (1)

Country Link
CH (1) CH220960A (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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