DE2507576A1 - 2-Oxo-1-pyrrolidinylacetamide of high purity - prepd. from 1-chloro-methyl-2-pyrrolidone with copper cyanide and partial hydrolysis with ion exchange resin - Google Patents
2-Oxo-1-pyrrolidinylacetamide of high purity - prepd. from 1-chloro-methyl-2-pyrrolidone with copper cyanide and partial hydrolysis with ion exchange resinInfo
- Publication number
- DE2507576A1 DE2507576A1 DE19752507576 DE2507576A DE2507576A1 DE 2507576 A1 DE2507576 A1 DE 2507576A1 DE 19752507576 DE19752507576 DE 19752507576 DE 2507576 A DE2507576 A DE 2507576A DE 2507576 A1 DE2507576 A1 DE 2507576A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- pyrrolidone
- exchange resin
- pyrrolidinylacetamide
- ion exchange
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
"Verfahren zur Herstellung eines N-substituierten Pyrrolidons" Die Erfindung bezieht sich auf ein neues Verfahren zur Herstellung eines N-substituierten Pyrrolidons, welches als 2-Oxo-l-pyrrolidinylacetamid bezeichnet wird und dessen Formel wie folgt ist: Dieser Stoff besitzt bemerkenswerte therapeutische Eigenschaften, nämlich eine selektive Wirkung auf die Großhirnrinde, wobei sie aktivierende, schützende und wiederherstellende Wirkungen auf die Nervenzellen ausübt."Process for the preparation of an N-substituted pyrrolidone" The invention relates to a new process for the preparation of an N-substituted pyrrolidone, which is referred to as 2-oxo-1-pyrrolidinylacetamide and whose formula is as follows: This substance has remarkable therapeutic properties, namely a selective effect on the cerebral cortex, with activating, protective and restorative effects on the nerve cells.
Das neue Verfahren ist außergewöhnlich einfach und liefert ein Zwischenprodukt und ein Endnrodukt in ausgezeichneter Qualität, wodurch sich Vorteile hinsichtlich des Preises des 2-Oxo-1-pyrrolidinylacetamids ergeben.The new process is exceptionally simple and provides an intermediate product and an end product of excellent quality, resulting in advantages in terms of the price of 2-oxo-1-pyrrolidinylacetamide result.
Als Ausgangsmaterial wird bei diesem Verfahren 1-Chloromethyl-2-pyrrolidon verwendet das durch Umsetzung von 1-Hydroxymethyl-2-pyrrolidon mit Thionylchlorid erhalten werden kann. Der erwähnte Stoff wird in einem geeigneten Lösungsmittel mit Kupfercyanid behandelt, worauf das Lösungsmittel abgedampft und das erhaltene 2-Oxo-1 -pyrrolidinylacetonitril im Vakuum destilliert wird. Dieses Nitril wird hierauf teilweise unter solchen Bedingungen hydrolysiert, daß nur das 2-Oxo-i-pyrrolidinylacetamid und nicht die entsprechende Säure entsteht. Dies kann durch die Verwendung eines Ionenaustauschharzes erreicht werden, welches die Hydrolyse ohne besondere Vorkehrungen beim gewünschten Hydrolysegrad anhält, wobei ein vollkommen reiner Stoff erhalten wird.The starting material used in this process is 1-chloromethyl-2-pyrrolidone uses this by reacting 1-hydroxymethyl-2-pyrrolidone with thionyl chloride can be obtained. The mentioned substance is in a suitable solvent treated with copper cyanide, whereupon the solvent evaporated and the obtained 2-oxo-1-pyrrolidinylacetonitrile is distilled in vacuo. This nitrile will then partially hydrolyzed under such conditions that only the 2-oxo-i-pyrrolidinylacetamide and the corresponding acid is not produced. This can be done by using a Ion exchange resin can be achieved, which allows hydrolysis without special precautions persists at the desired degree of hydrolysis, leaving a completely pure substance will.
Das Verfahren kann durch das folgende Schema dargestellt werden: Die Erfindung wird durch das nachstehende Beispiel näher erläutert.The procedure can be represented by the following scheme: The invention is illustrated in more detail by the example below.
B e i s p i e ] Herstellung des 2-Oxo-l-pyrrolidinylacetanids. B e i s p i e] Preparation of 2-oxo-l-pyrrolidinylacetanide.
a) 2-Oxo-l-pyrrolidinylacetonitril.a) 2-Oxo-1-pyrrolidinylacetonitrile.
In einen 10 1 fassenden Behälter, der in ein Eisbad eingetaucht und mit einem Rührer und einem Thermometer ausgerüstet ist, werden 350 ml (4,85 Mol) Thionylchlorid, das in 350 ml Dioxan gelöst ist, eingebracht. Die Lösung wird auf 0°C abgekühlt, und während das Reaktionsgemisch auf eine Temperatur unter 5 0C gehalten wird, wird eine Lösung von 510 g (4,45 Mol) l-Hydroxymethyl-2-pyrrolidon in 6,5 1 Dioxan im Verlaufe von 3 st zugegeben. Das Dioxan wird dann abdestilliert, Das 1-Chloromethyl-2-pyrrolidon bleibt in Form eines gelb-orangen Öls zurück. Sein Gewicht beträgt etwa 665 g.In a 10 liter container that is immersed in an ice bath and equipped with a stirrer and a thermometer, 350 ml (4.85 mol) Thionyl chloride, which is dissolved in 350 ml of dioxane, introduced. The solution will be on Cooled 0 ° C, and while the reaction mixture is kept at a temperature below 5 0C is, a solution of 510 g (4.45 mol) of l-hydroxymethyl-2-pyrrolidone in 6.5 1 dioxane was added over the course of 3 hours. The dioxane is then distilled off 1-chloromethyl-2-pyrrolidone remains in the form of a yellow-orange oil. Its weight is about 665 g.
Zu diesem Öl werden 4,5 1 Dioxan und 450 g Kupfercyanid zugegeben, worauf das Gemisch 3 st auf Rückfluß erhitzt wird. Das Gemisch wird dann abgekühlt und schließlich filtriert. Das Dioxan wird unter niedrigem Druck von der Lösung entfernt. Der Rückstand wird dann destilliert, und die zwischen 130 und 155 0C bei 1 bis 2 mm Druck übergehende Fraktion wird gesammelt.4.5 l of dioxane and 450 g of copper cyanide are added to this oil, whereupon the mixture is refluxed for 3 st. The mixture is then cooled and finally filtered. The dioxane is released from the solution under low pressure removed. The residue is then distilled, and between 130 and 155 0C at Fraction withstanding 1 to 2 mm of pressure is collected.
Es wird ein farbloses Ö1 erhalten, das beim Abkühlen annähernd 365 g rohes 2-Oxo-pyrrolidinylacetonitril in Form eines weißen kristallinen Feststoffs ergibt.A colorless oil is obtained which, on cooling, is approximately 365 g of crude 2-oxo-pyrrolidinylacetonitrile in the form of a white crystalline solid results.
b) 2-Oxo-l-pyrrolidinylacetamid.b) 2-oxo-1-pyrrolidinylacetamide.
248 g (2 Mol) rohes 2-Oxo-1-pyrrolidinylacetonitril werden in 2 1 Wasser aufgelöst. Nachdem 600 ml LEWATITF M 504 zugegeben worden sind, wird das Gemisch 2 st auf Rückfluß gehalten. Anschließend wird es abgekühlt und filtriert. Das Harz wird mit Wasser gewaschen, und die wäßrige Lösung wird eingedampft. Der Rückstand wird mit 1 1 Isopropanol behandelt. Dabei wird das 2-Oxo-l-pyrrolidinylacetamid in einem sehr reinen Zustand und in Form eines kristallinen Feststoffs erhalten, der nach dem Abfiltrieren und Trocknen 192 g wiegt und bei 151 bis 1520C schmilzt.248 g (2 mol) of crude 2-oxo-1-pyrrolidinylacetonitrile are in 2 1 Dissolved in water. After 600 ml of LEWATITF M 504 have been added, the Mixture 2 st Held at reflux. It is then cooled down and filtered. The resin is washed with water and the aqueous solution is evaporated. The residue is treated with 1 l of isopropanol. This is the 2-oxo-l-pyrrolidinylacetamide obtained in a very pure state and in the form of a crystalline solid, which after filtering off and drying weighs 192 g and melts at 151 to 1520C.
PATENTANSPRÜCHE:PATENT CLAIMS:
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES42433274 | 1974-03-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2507576A1 true DE2507576A1 (en) | 1975-09-11 |
Family
ID=8466228
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752507576 Withdrawn DE2507576A1 (en) | 1974-03-07 | 1975-02-21 | 2-Oxo-1-pyrrolidinylacetamide of high purity - prepd. from 1-chloro-methyl-2-pyrrolidone with copper cyanide and partial hydrolysis with ion exchange resin |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS50123666A (en) |
AR (1) | AR204442A1 (en) |
DE (1) | DE2507576A1 (en) |
FI (1) | FI750507A (en) |
NL (1) | NL7407140A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069336A (en) * | 1976-02-25 | 1978-01-17 | Chemisches Laboratorium Fritz-Walter Lange Gmbh & Co Kg | (2-oxo-pyrrolidines)-acetic hydrazides |
US4145347A (en) * | 1977-03-03 | 1979-03-20 | Parke, Davis & Company | N-(substituted-aminoalkyl)-2-oxo-1-pyrrolidineacetamides |
US4162325A (en) * | 1976-10-22 | 1979-07-24 | Ucb, Societe Anonyme | N-substituted lactams |
EP0307423A1 (en) * | 1987-03-20 | 1989-03-22 | Gaf Chemicals Corporation | Manufacture of haloalkyl lactams |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5442330B2 (en) * | 1973-09-01 | 1979-12-13 |
-
1974
- 1974-05-28 NL NL7407140A patent/NL7407140A/en not_active Application Discontinuation
-
1975
- 1975-01-01 AR AR25788175A patent/AR204442A1/en active
- 1975-02-21 DE DE19752507576 patent/DE2507576A1/en not_active Withdrawn
- 1975-02-24 FI FI750507A patent/FI750507A/fi not_active Application Discontinuation
- 1975-03-04 JP JP2640875A patent/JPS50123666A/ja active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069336A (en) * | 1976-02-25 | 1978-01-17 | Chemisches Laboratorium Fritz-Walter Lange Gmbh & Co Kg | (2-oxo-pyrrolidines)-acetic hydrazides |
US4162325A (en) * | 1976-10-22 | 1979-07-24 | Ucb, Societe Anonyme | N-substituted lactams |
US4145347A (en) * | 1977-03-03 | 1979-03-20 | Parke, Davis & Company | N-(substituted-aminoalkyl)-2-oxo-1-pyrrolidineacetamides |
EP0307423A1 (en) * | 1987-03-20 | 1989-03-22 | Gaf Chemicals Corporation | Manufacture of haloalkyl lactams |
EP0307423A4 (en) * | 1987-03-20 | 1990-12-05 | Gaf Corporation | Manufacture of haloalkyl lactams |
Also Published As
Publication number | Publication date |
---|---|
FI750507A (en) | 1975-09-08 |
NL7407140A (en) | 1975-09-09 |
JPS50123666A (en) | 1975-09-29 |
AR204442A1 (en) | 1976-02-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8139 | Disposal/non-payment of the annual fee |