DE838291C - Process for the production of basic ethers of benzhydrol - Google Patents
Process for the production of basic ethers of benzhydrolInfo
- Publication number
- DE838291C DE838291C DESCH1876A DESC001876A DE838291C DE 838291 C DE838291 C DE 838291C DE SCH1876 A DESCH1876 A DE SCH1876A DE SC001876 A DESC001876 A DE SC001876A DE 838291 C DE838291 C DE 838291C
- Authority
- DE
- Germany
- Prior art keywords
- benzhydrol
- production
- basic ethers
- ethers
- basic
- 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.)
- Expired
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
- C07D295/04—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Description
Verfahren zur Herstellung von basischen Äthern des Benzhydrols Gegenstand des Patents 833 igo ist ein Verfahren zur Herstellung von Äthern, zu denen man gelangt, wenn man Alkohole der aliphatischen und aliphatisch-aromatischen Reihe mit aromatischen Sulfonsäuren, gegebenenfalls in Lösungs- und/oder Verdünnungsmitteln, erhitzt. Die dort beschriebenen Verbindungen zeichneten sich als Pharmaceutica durch eine gute @Xntihistaminwirkung aus.Process for the preparation of basic ethers of benzhydrol subject of the patent 833 igo is a process for the production of ethers, which one arrives at when you mix alcohols of the aliphatic and aliphatic-aromatic series with aromatic Sulphonic acids, optionally in solvents and / or diluents, heated. the Compounds described there stood out as Pharmaceutica by a good @Xntihistamine effect.
Bei der Weiterbearbeitung wurde nun gefunden, daß man auch basische lieterocvclische Aminoalkohole mit aliphatisch-aromatischen Alkoholen mittels aromatischen Sulfonsäureti zu Äthern umsetzen kann. Dieses war nicht ohne weiteres vorauszusehen, da heterocyclische Verbindungen unter den hier angewandten Bedingungen zu tiefer greifenden Zersetzurigen führen können. Man kann die Reaktion auch in Anwesenheit von Lösungs- und/oder Verdünnungsmitteln durchführen. Diese Reaktionsprodukte zeigen gegenüber dem in Patent 833 190 beschriebenen Dimethylaminoäthylbenzhydryläther bei gleicher Toxizität eine viermal größere Wirksamkeit, was bei Verwendung des Pyrrolidinringes als basischen heterocyclischen Restes der Fall ist. Beispiel a Gewichtsteile N-Pyrrolidyläthanol werden mit den gleichen Teilen Benzhydrol und 4 bis 5 Gewichtsteilen Toluolsulfonsäure etwa a Stunden auf dem Wasserbad unter Rühren erhitzt. Dann wird die Schmelze auf Eis gegossen und mit Natronlauge alkalisch gemacht. Die Base wird dann in Toluol aufgenommen, und die Toluollösung wird .mit geglühter Pottasche getrocknet. Durch Einleiten von Chlorwasserstoffgas in die filtrierte Toluollösung erhält man in guter Ausbeute das Hydrochlorid des Pyrrolidyläthylbenzhydryläthers in feinen Kristallen vom Schmelzpunkt i26°.In further processing it has now been found that one can also use basic Lieterocvclic amino alcohols with aliphatic-aromatic alcohols by means of aromatic Sulfonsäureti can convert to ethers. This could not be foreseen without further ado, because heterocyclic compounds too deep under the conditions used here can lead to pervasive decomposition. The reaction can also be seen in the presence of solvents and / or thinners. These reaction products show compared to the dimethylaminoethylbenzhydryl ether described in patent 833 190 with the same toxicity, a four times greater effectiveness, which when using the Pyrrolidine ring as a basic heterocyclic radical is the case. Example a Parts by weight of N-pyrrolidylethanol are used with equal parts of benzhydrol and 4 to 5 parts by weight of toluenesulfonic acid on the water bath for about a hour Stirring heated. Then the melt is poured onto ice and covered with caustic soda alkaline made. The base is then taken up in toluene, and the toluene solution is .mit dried annealed potash. By introducing hydrogen chloride gas into the filtered Toluene solution gives the hydrochloride of pyrrolidylethylbenzhydrylether in good yield in fine crystals with a melting point of 26 °.
Setzt man dem obigen Ansatz noch etwa 2o bis 30 Gewichtsteile Toluol als Lösungs- bzw. Verdünnungsmittel hinzu, so erhält marn nach der gleichen Aufarbeitung, wie oben angegeben, die neue Substanz in guter Ausbeute.If about 20 to 30 parts by weight of toluene are added to the above approach as a solvent or diluent, the new substance is obtained in good yield after the same work-up as indicated above.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH1876A DE838291C (en) | 1950-04-22 | 1950-04-22 | Process for the production of basic ethers of benzhydrol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH1876A DE838291C (en) | 1950-04-22 | 1950-04-22 | Process for the production of basic ethers of benzhydrol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE838291C true DE838291C (en) | 1952-05-08 |
Family
ID=7423056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH1876A Expired DE838291C (en) | 1950-04-22 | 1950-04-22 | Process for the production of basic ethers of benzhydrol |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE838291C (en) |
-
1950
- 1950-04-22 DE DESCH1876A patent/DE838291C/en not_active Expired
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