CH297713A - 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
- CH297713A CH297713A CH297713DA CH297713A CH 297713 A CH297713 A CH 297713A CH 297713D A CH297713D A CH 297713DA CH 297713 A CH297713 A CH 297713A
- Authority
- CH
- Switzerland
- Prior art keywords
- nicotinic acid
- preparation
- acid amide
- ethyl
- new
- Prior art date
Links
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 1-ethyl Chemical group 0.000 claims description 4
- 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
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-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
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 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
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines neuen disubstituierten Nicotinsäureamids. Gegenstand der Erfindung ist.
ein Ver- 1'abren zur Herstellung eines neuen disubsti- tuierten Nicotinsäureamidss der Formel
EMI0001.0012
welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0013
deearboxyliert. Die Decarboxylierung kann durch Er- liitzen in An- oder Abwesenheit eines Lö- sunys- bzw. Verdünnungsmittels erfolgen.
Die Verbindung der Formel I kann bei- spielsweise durch Umsetzung von Chinolin- sHureanhycIrid mit N-(1,2 D,iphenyl-ätliyl)-N- (2-pil)eridino-äthyl)=amin gewonnen werden.
Es ist auch möglich, die gebildete Verbin- dLin.-- der Formel I ohne Isolierung zu de- e a rboxyIieren. Das so erhaltene Nieotinsäure-N-(1,2-di- phenyl-ät.hyl) -N- (2-pip eridino-äthyl) -amid bil det ein nahezu farbloses öl, welches unter 0,08 mm bei 2@5@0-260 siedet und sich gut in verdünnten Säuren, wenig in Wasser und Petroläther löst.
Das Chlorhydrat der Ver bindung schmilzt bei 170-176 , Die neue Verbindung soll als Spasmolyti- kum und als Zwischenprodukt zur Herstel- lnng weiterer Derivate Verwendung finden.
Beispiel: Zu 149 g geschmolzenem Chinolinsäure- anhydrid werden innert 10, Minuten 154 g N (1,2-Diphenyl-.äthyl)-N (2'-piperidino-ät-hyl)- amin zugetropft, wobei die 'Temperatur um 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. Natronlauge versetzt und 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-Salzsäure ausgezogen und der salzsaure Auszug eben falls mit Kohle behandelt, filtriert-, wieder alkalisch gemacht und erschöpfend ausge- äthert. Nach dem Verdampfen des Äthers und Destillieren des Rückstandes im Hochvakuum gewinnt, man das unter 0,08 mm bei 2!50-2.60 siedende Nicotinsäure=N-(1,2-diphenyl-äthyl)- -N-('31-piperidino-äthy-1)
-amid inbefriedigender Ausbeute.
Die neue Verbindung löst sich leicht in verdünnt-en Säuren, weniger gilt in Wasser und Petroläther. Das Chlorhydrat der Ver bindung schmilzt bei 170-176 .
Process for the preparation of a new disubstituted nicotinic acid amide. The subject of the invention is.
a procedure for the preparation of a new disubstituted nicotinic acid amide of the formula
EMI0001.0012
which is characterized in that the compound of the formula
EMI0001.0013
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 quinoline-sHureanhycIrid with N- (1,2 D, iphenyl-ethyl) -N- (2-pil) eridino-ethyl) = amine.
It is also possible to de-arboxyIieren the compound formed - the formula I without isolation. The resulting nieotinic acid-N- (1,2-diphenyl-ethyl) -N- (2-pip eridino-ethyl) -amide forms an almost colorless oil, which is below 0.08 mm at 2 @ 5 @ 0-260 boils and dissolves well in dilute acids, little in water and petroleum ether.
The hydrochloride of the compound melts at 170-176. The new compound is said to be used as an antispasmodic and as an intermediate for the production of further derivatives.
Example: 154 g of N (1,2-diphenyl-ethyl) -N (2'-piperidino-ethyl) -amine are added dropwise to 149 g of molten quinolinic anhydride within 10 minutes, the temperature being reduced by about 30 increases. Then heated. one 15 minutes to 160 and then allowed to cool the melt. The glassy solidified mass is dissolved in 2N hydrochloric acid with. Sodium hydroxide solution is added and the mixture is extracted with chloroform.
The chloroform is evaporated after drying over sodium sulfate. Solve it. the residue - a black, thick syrup - in ether, treated with charcoal and filtered. The filtrate. will with. 2N hydrochloric acid extracted and the hydrochloric acid extract also treated with charcoal, filtered, made alkaline again and exhaustively etherified. After evaporation of the ether and distillation of the residue in a high vacuum, nicotinic acid = N- (1,2-diphenyl-ethyl) - -N - ('31-piperidino- (' 31-piperidino- boiling below 0.08 mm at 2.50-2.60 ethy-1)
-amid in a satisfactory yield.
The new compound dissolves easily in dilute acids, less so in water and petroleum ether. The hydrochloride of the compound melts at 170-176.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297713T | 1951-03-01 | ||
| CH297720T | 1951-03-01 | ||
| CH293815T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297713A true CH297713A (en) | 1954-03-31 |
Family
ID=27178190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297713D CH297713A (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) | CH297713A (en) |
-
1951
- 1951-03-01 CH CH297713D patent/CH297713A/en unknown
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