DE83524C - - Google Patents
Info
- Publication number
- DE83524C DE83524C DENDAT83524D DE83524DA DE83524C DE 83524 C DE83524 C DE 83524C DE NDAT83524 D DENDAT83524 D DE NDAT83524D DE 83524D A DE83524D A DE 83524DA DE 83524 C DE83524 C DE 83524C
- Authority
- DE
- Germany
- Prior art keywords
- piperazine
- hydrochloric acid
- acid
- parts
- dinitrosodiphenylpiperazine
- 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.)
- Active
Links
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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Printing Methods (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT. Y&PATENT OFFICE. Y &
In dem Patent Nr. 60547 wurde gezeigt, dafs bei der Einwirkung von Alkalien auf Dinitrosodiphenylpiperazin Piperazin abgespalten wird. Es wurde nun weiter gefunden, dafs sich an Stelle der Alkalien auch Säuren, wie z. B. Salzsäure, zur Zerlegung des Dinitrosodiphenylpiperazins behufs Darstellung von Piperazin verwenden lassen. Dinitrosodiphenylpiperazin verhält sich sonach der Salzsäure gegenüber nicht analog wie das Nitrosodimethylanilin, denn letzteres liefert beim Erhitzen mit Salzsäure kein Dimethylamin, sondern geht dabei, wie Möhlau (vgl. Berichte XIX, S. 2010) festgestellt hat, in ein Gemisch von Dimethyl-p-phenylendiamin, Dimethyl-p-dichlor-p-phenylendiamin und p-Dichlor-p-phenylendiamin über. ·In the patent No. 60547 it was shown that when exposed to alkalis, Dinitrosodiphenylpiperazin piperazine is split off. It has now been further found that Instead of alkalis, acids such as B. hydrochloric acid, for the decomposition of dinitrosodiphenylpiperazine let use for the preparation of piperazine. Dinitrosodiphenylpiperazine behaves accordingly Hydrochloric acid is not analogous to nitrosodimethylaniline, because the latter delivers when heated with hydrochloric acid, no dimethylamine, but, as Möhlau (cf. Reports XIX, p. 2010) in a mixture of dimethyl-p-phenylenediamine, dimethyl-p-dichloro-p-phenylenediamine and p-dichloro-p-phenylenediamine over. ·
Zur Darstellung des Piperazine wird im allgemeinen in der Weise verfahren, dafs entweder die frisch dargestellte Dinitrosodiphenylpiperazinpaste mit der verdünnten Säure angeschlemmt und die resultirende Flüssigkeit so lange gekocht wird, bis die Dinitrosoverbindung vollständig zersetzt ist, oder indem einfach die bei der Nitrosirung des Diphenylpiperazins resultirende saure Lösung der Dinitrosoverbindung bis zur erfolgten Zersetzung eingekocht wird.For the preparation of the piperazine is generally in such a way that either the freshly prepared Dinitrosodiphenylpiperazinpaste with the dilute acid slurried and the resulting liquid is boiled until the dinitroso compound is completely decomposed, or simply by the nitrosation of diphenylpiperazine The resulting acidic solution of the dinitroso compound is boiled down until decomposition has taken place.
ι Gewichtstheil einer 12 proc. Dinitrosodiphenylpiperazinpaste wird mit 1 Gewichtstheil Salzsäure (200 B.) und 30 Theilen Wasser 2 Stunden lang unter Ersatz des verdampfenden Wassers gekocht. Man fütrirt, setzt zum Filtrat die der angewendeten Säure entsprechende Menge Soda, fütrirt nochmals von einem geringen Niederschlage ab, setzt einen kleinen Ueberschufs Natron hinzu und destillirt die Flüssigkeit aus dem Oelbade ab. Das Destillat wird mit Salzsäure eingedampft und so salzsaures Piperazin erhalten, das in bekannter Weise auf Piperazinbase verarbeitet wird. Die Ausbeuten sind gut.ι part by weight of a 12 per cent. Dinitrosodiphenylpiperazinpaste is cooked with 1 part by weight of hydrochloric acid (20 0 B.) and 30 parts of water for 2 hours with the replacement of the evaporating water. The mixture is fed, the amount of soda corresponding to the acid used is added to the filtrate, a small amount of precipitate is removed again, a small excess of soda is added, and the liquid is distilled off from the oil bath. The distillate is evaporated with hydrochloric acid and thus hydrochloric acid piperazine is obtained, which is processed in a known manner on the piperazine base. The yields are good.
An Stelle der Salzsäure können im vorstehenden Beispiel auch andere Mineralsäuren, wie Schwefelsäure, Phosphorsäure, ferner" organische Säuren, wie z. B. Oxalsäure und Essigsäure, Verwendung finden.Instead of hydrochloric acid, other mineral acids, like sulfuric acid, phosphoric acid, furthermore " organic acids such as B. oxalic acid and acetic acid, use.
ι Theü Diphenylpiperazin wird in 700 Theilen Wasser und einem Gemisch von 8,3 Theilen Salzsäure von 20 ° B. und 4,65 Theilen Schwefelsäure von 66° B. gelöst und mit 0,62 Theilen Natriumnitrit nitrosirt. Man filtrirt von etwas Harz ab und kocht das Filtrat bis auf ca. zwei Drittel seines ursprünglichen Volumens ein; hierbei scheidet sich ein schwarzer Niederschlag ab, die anfangs lebhaft grüngelbe Flüssigkeit nimmt einen röthlich mifsfarbigen Ton an, und in einer filtrirten Probe derselben läfst sich jetzt bereits das Piperazin nachweisen. Ohne zu fütriren, ver-ι Theü is diphenylpiperazine in 700 parts Water and a mixture of 8.3 parts of hydrochloric acid of 20 ° B. and 4.65 parts of sulfuric acid of 66 ° B. dissolved and with 0.62 parts of sodium nitrite are nitrosated. Some resin is filtered off, and the filtrate is boiled down to about two thirds of its original volume; here one separates black precipitate, the initially lively greenish-yellow liquid takes on a reddish color mif-colored tone, and in a filtered sample of it this can already be done Detect piperazine. Without leading,
setzt man das Reactionsgemisch mit der der angewendeten Schwefelsäure entsprechenden Menge Schlemmkreide oder Bariumcarbonat, filtrirt, kocht das Filtrat auf ein geringes Volumen ein, setzt das Piperazin durch Natron in Freiheit und destillirt es im Dampfstrom über. Aus dem Destillat läfst sich das Piperazin in der üblichen Weise gewinnen.the reaction mixture is set with that corresponding to the sulfuric acid used A lot of chalk or barium carbonate, filtered, and the filtrate boils to a low level Volume, sets the piperazine free by means of soda and distills it in a stream of steam above. The piperazine can be obtained from the distillate in the usual way.
Das Dinitrosodiphenylpiperazin kann durch seine Homologen ersetzt werden.The dinitrosodiphenylpiperazine can be replaced by its homologues.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE63618T |
Publications (1)
Publication Number | Publication Date |
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DE83524C true DE83524C (en) |
Family
ID=32857101
Family Applications (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT77351D Active DE77351C (en) | Process for the preparation of piperazine | ||
DENDAT71576D Expired - Lifetime DE71576C (en) | Process for the preparation of piperazine. (3 | ||
DENDAT79121D Expired - Lifetime DE79121C (en) | Process for the preparation of piperazine | ||
DENDAT83524D Active DE83524C (en) | |||
DENDAT65347D Expired - Lifetime DE65347C (en) | Process for the preparation of piperazine. (2 | ||
DENDAT60547D Expired - Lifetime DE60547C (en) | Process for the preparation of piperazine | ||
DENDAT63618D Expired - Lifetime DE63618C (en) | Process for the production of piperazine | ||
DENDAT98031D Active DE98031C (en) |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT77351D Active DE77351C (en) | Process for the preparation of piperazine | ||
DENDAT71576D Expired - Lifetime DE71576C (en) | Process for the preparation of piperazine. (3 | ||
DENDAT79121D Expired - Lifetime DE79121C (en) | Process for the preparation of piperazine |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT65347D Expired - Lifetime DE65347C (en) | Process for the preparation of piperazine. (2 | ||
DENDAT60547D Expired - Lifetime DE60547C (en) | Process for the preparation of piperazine | ||
DENDAT63618D Expired - Lifetime DE63618C (en) | Process for the production of piperazine | ||
DENDAT98031D Active DE98031C (en) |
Country Status (1)
Country | Link |
---|---|
DE (8) | DE98031C (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2415785A (en) * | 1943-02-24 | 1947-02-11 | Burroughs Wellcome Co | Unsymmetrically substituted piperazines |
CA1331757C (en) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
-
0
- DE DENDAT77351D patent/DE77351C/en active Active
- DE DENDAT71576D patent/DE71576C/en not_active Expired - Lifetime
- DE DENDAT79121D patent/DE79121C/en not_active Expired - Lifetime
- DE DENDAT83524D patent/DE83524C/de active Active
- DE DENDAT65347D patent/DE65347C/en not_active Expired - Lifetime
- DE DENDAT60547D patent/DE60547C/en not_active Expired - Lifetime
- DE DENDAT63618D patent/DE63618C/en not_active Expired - Lifetime
- DE DENDAT98031D patent/DE98031C/de active Active
Also Published As
Publication number | Publication date |
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DE77351C (en) | |
DE79121C (en) | |
DE60547C (en) | |
DE98031C (en) | |
DE63618C (en) | |
DE71576C (en) | |
DE65347C (en) |
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