CH297710A - Process for the preparation of a new disubstituted nicotinic acid amide. - Google Patents
Process for the preparation of a new disubstituted nicotinic acid amide.Info
- Publication number
- CH297710A CH297710A CH297710DA CH297710A CH 297710 A CH297710 A CH 297710A CH 297710D A CH297710D A CH 297710DA CH 297710 A CH297710 A CH 297710A
- Authority
- CH
- Switzerland
- Prior art keywords
- nicotinic acid
- preparation
- new
- acid amide
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- VCOJCHSIJXOYNQ-UHFFFAOYSA-N CCN(CC)CCCN(C(CC1=CC=CC=C1)C1=CC=CC=C1)C(C1=CN=CC=C1)=O Chemical compound CCN(CC)CCCN(C(CC1=CC=CC=C1)C1=CC=CC=C1)C(C1=CN=CC=C1)=O VCOJCHSIJXOYNQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 2
- -1 diethylamino-propyl Chemical group 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MQOFTYLTYOIKJL-UHFFFAOYSA-N n-(1,2-diphenylethyl)-n',n'-diethylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1C(NCCCN(CC)CC)CC1=CC=CC=C1 MQOFTYLTYOIKJL-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen disubatituierten Nicotinsäureamids. Gegenstand der Erfindung ist. ein Verfah ren zur Herstellung eines neuen disubstituier- ten Nicotinsäureamids der Formel
EMI0001.0006
welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0007
deearboxyliert. Die Decarboxylierung kann durch Erhit zen in An- oder Abwesenheit eines Lösungs- bzw. Verdünnungsmittels erfolgen.
Die Verbindung der Formel I kann bei spielsweise durch Umsetzung von Chinolin- säureanltydrid mit :%T-(1,2-Diphenyl-ä.thyl)-N- (diäthylamino-propyl)-amin gewonnen wer den. (;s ist auch möglich, die gebildete Ver- bindung der Formel I ohne Isolierung zu decarboxylieren.
Das so erhaltene Nicotinsäure-N-(1,2-di- phenyl-äthyl)-N-(diäthylamino-propyl)-amid bildet ein nahezu farbloses Öl, welches unter 0,15 mm bei 235-240 siedet und sich gut in verdünnten Säuren, wenig in Wasser und Petroläther löst. Das Chlorhydrat der Ver bindung schmilzt aus Methyl-isobutylketon umkristallisiert bei etwa 50-70 und ist amorph.
Die neue Verbindung soll als Spasmolyti- kum und als Zwischenprodukt zur Herstel lung weiterer Derivate Verwendung finden. <I>Beispiel:</I> Zu 75 g geschmolzenem Chinolinsäure- anhydrid werden innert 15 Minuten 77,5 g N-(1,2-Diphenyl-äthyl)-N-(diäthylamino-pro- pyl)-amin zugetropft, wobei die Temperatur lun etwa 30 steigt. Anschliessend erhitzt man 15 Minuten auf 160 und lässt darnach die Schmelze erkalten.
Die glasig erstarrte Masse wird in 2n-Salzsäure gelöst, mit Natroilauge versetzt lind mit Chloroform extrahiert. Das Chloroform wird nach dem Trocknen über Natriumsulfat, verdampft. Darauf löst man den Rückstand - einen schwarzen, dicken Sirup - in Äther, behandelt mit Kohle und filtriert.
Das Filtrat wird mit 2n-Salzsäiire ausgezogen und der salzsaure Auszug eben falls mit Kohle behandelt, filtriert, wieder alkalisch gemacht und erschöpfend ausge- ä.thert. Nach dem Verdampfen des Äthers und Destillieren des Rückstandes im Hochvakuiun gewinnt man das unter 0,15 mm bei 235 bis 2400 siedende Nicotinsäure-N-(1,2-diphenyl- ä.t.hyl)-N-(cliäthylamino-propyl)-amid in be friedigender Ausbeute.
Die neue Verbindung löst sich leicht in verdünnten Säuren, weniger gut in Wasser Lind Petroläther. Das Chlorhydrat der Ver bindung schmilzt aus 3lethylisobuty lketon umkristallisiert bei etwa 50-70 und ist amorph.
Process for the preparation of a new disubstituted nicotinic acid amide. The subject of the invention is. a process for the preparation of a new disubstituted nicotinic acid amide of the formula
EMI0001.0006
which is characterized in that the compound of the formula
EMI0001.0007
deearboxylated. The decarboxylation can be carried out by heating in the presence or absence of a solvent or diluent.
The compound of the formula I can be obtained, for example, by reacting quinolinic acid anltydride with:% T- (1,2-diphenyl-Ä.thyl) -N- (diethylamino-propyl) amine. It is also possible to decarboxylate the compound of the formula I formed without isolation.
The nicotinic acid-N- (1,2-diphenyl-ethyl) -N- (diethylamino-propyl) -amide obtained in this way forms an almost colorless oil which boils below 0.15 mm at 235-240 and is well diluted Acids, little dissolves in water and petroleum ether. The chlorohydrate of the compound melts from methyl isobutyl ketone recrystallized at about 50-70 and is amorphous.
The new compound is said to be used as an antispasmodic and as an intermediate for the production of further derivatives. <I> Example: </I> To 75 g of molten quinolinic anhydride, 77.5 g of N- (1,2-diphenyl-ethyl) -N- (diethylamino-propyl) -amine are added dropwise within 15 minutes, whereby the temperature rises by about 30. The mixture is then heated to 160 for 15 minutes and then allowed to cool the melt.
The glassy solidified mass is dissolved in 2N hydrochloric acid, sodium hydroxide solution is added and extracted with chloroform. After drying over sodium sulfate, the chloroform is evaporated. The residue - a thick black syrup - is then dissolved in ether, treated with charcoal and filtered.
The filtrate is extracted with 2N hydrochloric acid and the hydrochloric acid extract is also treated with charcoal, filtered, made alkaline again and thoroughly aethered. After evaporation of the ether and distillation of the residue in a high vacuum, nicotinic acid-N- (1,2-diphenyl- Ä.t.hyl) -N- (diethylamino-propyl) - is obtained, boiling below 0.15 mm at 235 to 2400 amide in satisfactory yield.
The new compound dissolves easily in dilute acids, less so in water and petroleum ether. The chlorohydrate of the compound melts from 3lethylisobutylketon recrystallized at about 50-70 and is amorphous.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297720T | 1951-03-01 | ||
| CH297710T | 1951-03-01 | ||
| CH293815T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297710A true CH297710A (en) | 1954-03-31 |
Family
ID=27178187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297710D CH297710A (en) | 1951-03-01 | 1951-03-01 | Process for the preparation of a new disubstituted nicotinic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297710A (en) |
-
1951
- 1951-03-01 CH CH297710D patent/CH297710A/en unknown
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