CH194109A - Process for the preparation of the 2 ', 6'-dimethylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid. - Google Patents
Process for the preparation of the 2 ', 6'-dimethylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid.Info
- Publication number
- CH194109A CH194109A CH194109DA CH194109A CH 194109 A CH194109 A CH 194109A CH 194109D A CH194109D A CH 194109DA CH 194109 A CH194109 A CH 194109A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- isoxazole
- carboxylic acid
- preparation
- dimethylpiperidide
- Prior art date
Links
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 claims description 3
- 230000003555 analeptic effect Effects 0.000 claims description 3
- 239000002269 analeptic agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical class OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MPYGFFPGJMGVSW-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC1=NOC(C)=C1C(Cl)=O MPYGFFPGJMGVSW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 N-monosubstituted urethanes Chemical class 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Darstellung des 2',6'-Dnmethylpiperidids der 3,6-Dimethyl-isogazol-4-carbonsäure. Durch Umwandlung von Verbindungen der allgemeinen Formel
EMI0001.0003
in welcher einer der Reste Ri, R2, R3 eine Carboxylgruppe, die übrigen Alkylreste oder Wasserstoff bedeuten, in umsetzungsfähige Säureabkömmlinge, z. B.
Säurechloride und Umsetzung dieser Verbindungen mit sekun dären Aminen, erhält man dialkylsubstituierte Amide von Isoxazolcarbonsäuren, welche wertvolle therapeutische Eigenschaften auf weisen.
Es wurde nun gefunden, dass auch andere Verbindungen mit einer acylierbaren Imino- gruppe awidartige Verbindungen mit Isoxa- zolcarbonsäuren eingehen, die eine hervor ragende analeptische Wirkung aufweisen. Zu diesen Iminoverbindungen gehören sekundäre Amine der aromatischen Reihe, heterocyclische Verbindungen mit einer Iminogruppe, sowie N-monosubstituierte Urethane.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des 2',6'- Dimethylpiperidids der 3,5-Dimethyl-isoxa- zol-4-carbonsäure, welches dadurch gekenn zeichnet ist, dass man 3,5-Dimethyl-isoxazol- 4-carbonsäure, ein Kondensationsmittel und 2,6-Dimethylpiperidin aufeinander einwirken lässt.
Das neue 2',6'-Dimethylpiperidid der 3,5 Dimethyl-isoxazol-4-carbonsäure, welches als Arzneimittel verwendet werden soll, siedet bei 192-l95 und 11 mm und bildet ein in Wasser schwer lösliches Öl. Die analeptische Wirksamkeit ist etwa die gleiche wie die des 2'-1flethylpiperidids der 3,5-Dimethyl- isoxazol-4-carbonsäure. <I>Beispiel:</I> 142 Teile 3,5-Dimethyl-isoxazol-4-carbon- säure und 210 Teile Thionylchlorid werden unter Rückfluss auf dem Dampfbad erwärmt.
Nach Beendigung der Reaktion wird im Vakuum destilliert. Von dem erhaltenen 3,5 Dimethyl-isoxazol-4-carbonsäurechlorid wer den 159 Teile unter Kühlung und Rühren zu einer Mischung von 109 Teilen 2,6-Dimethyl- piperidin, 500 Teilen Benzol und 200 Teilen 20 o/oiger Natronlauge zutropfen gelassen. Die Benzolschicbt wird abgehoben, über wasser freier Pottasche getrocknet und der nach dem Abdampfen des Benzols verbleibende Rück stand im Vakuum destilliert.
Das 2',6'-Di- methyl-piperidid der 3,5-Dimethyl-isoxazol-4- carbonsäure destilliert bei 192-195o und 11 mm Druck.
Process for the preparation of the 2 ', 6'-dimethylpiperidide of 3,6-dimethyl-isogazole-4-carboxylic acid. By converting compounds of the general formula
EMI0001.0003
in which one of the radicals Ri, R2, R3 is a carboxyl group, the remaining alkyl radicals or hydrogen are converted into reactive acid derivatives, e.g. B.
Acid chlorides and reaction of these compounds with secondary amines, dialkyl-substituted amides of isoxazole carboxylic acids are obtained, which have valuable therapeutic properties.
It has now been found that other compounds with an acylatable imino group also enter into resistant compounds with isoxazolecarboxylic acids, which have an excellent analeptic effect. These imino compounds include secondary amines of the aromatic series, heterocyclic compounds with an imino group, and N-monosubstituted urethanes.
The subject of the present patent is a process for the preparation of the 2 ', 6'-dimethylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid, which is characterized in that 3,5-dimethyl-isoxazole 4- carboxylic acid, a condensing agent, and 2,6-dimethylpiperidine interact.
The new 2 ', 6'-dimethylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid, which is to be used as a drug, boils at 192-195 and 11 mm and forms an oil that is sparingly soluble in water. The analeptic effectiveness is about the same as that of 2'-1-methylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid. <I> Example: </I> 142 parts of 3,5-dimethyl-isoxazole-4-carboxylic acid and 210 parts of thionyl chloride are heated under reflux on the steam bath.
After the reaction has ended, it is distilled in vacuo. Of the 3,5-dimethyl-isoxazole-4-carboxylic acid chloride obtained, 159 parts are added dropwise, with cooling and stirring, to a mixture of 109 parts of 2,6-dimethylpiperidine, 500 parts of benzene and 200 parts of 20% sodium hydroxide solution. The benzene layer is removed, dried over anhydrous potash and the residue remaining after the benzene has evaporated is distilled in vacuo.
The 2 ', 6'-dimethyl-piperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid distilled at 192-195 ° and 11 mm pressure.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH185280T | 1936-01-24 | ||
| CH194109T | 1936-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194109A true CH194109A (en) | 1937-11-15 |
Family
ID=25721187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194109D CH194109A (en) | 1936-01-24 | 1936-03-20 | Process for the preparation of the 2 ', 6'-dimethylpiperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194109A (en) |
-
1936
- 1936-03-20 CH CH194109D patent/CH194109A/en unknown
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