CH297726A - 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
- CH297726A CH297726A CH297726DA CH297726A CH 297726 A CH297726 A CH 297726A CH 297726D A CH297726D A CH 297726DA CH 297726 A CH297726 A CH 297726A
- Authority
- CH
- Switzerland
- Prior art keywords
- nicotinic acid
- amide
- acid amide
- preparation
- ethyl
- Prior art date
Links
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)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellunu eines neuen disubstituierten Nicotinsäureamids. Gegenstand der Erfindung ist ein Ver fahren zur Herstellung eines neuen disubsti- tuierten Nicotinsäureamids der Formel
EMI0001.0007
ivelehes dadurch gekennzeichnet. ist, dass man einen reaktionsfähigen Ester des Alkohols der Formel
EMI0001.0014
mit. einer den Rest
EMI0001.0016
liefernden Verbindung umsetzt.
Als reaktionsfähige Ester des Alkohols I kann man beispielsweise einen Halogenwas- serstoffsä:ure-, einen Schwefelsäure-, einen Alkyl- bzw. Arylsulfonsäirreester verwenden. Statt des freien Aminoalkoholesters kann auch ein Salz eines solchen zur Reaktion ge bracht werden.
Vorteilhaft verwendet man als den Rest 1I liefernde Verbindung ein N-Metallderivat des 1I entsprechenden Amids. Man kann aber auch das freie Amid II unter Zuhilfenahme eines Metallamids als Kondensationsmittel mit einem reaktionsfähigen Aminoalkoholester zur Reaktion bringen.
Das so erhaltene Nicot.insäure-N-(1,2-di- phenyl-äthyl) -N -(ss-2;6-dimethyl-piperidino- äthyl)-amid löst sich gut in verdünnten Säu ren, wenig in Wasser und Petroläther. Die neue Verbindung soll als Spasmolytikum und als Zwischenprodukt. zur Herstellung weiterer Derivate Verwendung finden.
Beispiel: 15,1 g Nicotinsäure-N- (1,2-diphenyl-äthyl)- amid, suspendiert in 150 em3 absol. Benzol, werden mit 2,3 g gepulvertem Natriumamid versetzt und kurze Zeit auf Siedetemperatur erhitzt, wobei eine starke Ammoniakentwick- lung eintritt.
Nachdem die Gasentwicklung nachgelassen hat, lässt man 9,6 g ss-2,6-Di- methyl - piperidino - äthylehlorid, gelöst in 150 cms absol. Benzol, zutropfen und rührt dann weitere 10 Stunden unter Rückfluss- kochen. Nach dem Erkalten wird die Lösung vom überschüssigen Natriumamid abdekan- tiert und mit 60 warmer 1,5n-Salzsäure aus- gezogen, bis der Auszug sehwach sauer reagiert.
Der noch warme salzsaure Auszug wird mit. Kohle filtriert, mit Lauge. alkali- siert, .erschöpfend ausgeäthert und der Alther abdestilliert. Der Rückstand wird im Hoch v akuum destilliert, wobei das Nicotinsäur e-N- (1,2-diphenyl-äthy 1) -N- (ss-2, 6-dimethyl-piperi- dino-äthyl)-amid in guter Ausbeute gewonnen wird.
An Stelle von Natriumamid als Konden sationsmittel kann man das Nicotinsäure-N- (1,2-diphenyl-'äthyl)-amid mit Natrium be handeln und das entstandene Natriumsalz an schliessend mit ss-2,6-Dimethi-l-piperidino- äthy ichlorid kondensieren, wobei die Bleiehe Verbindung in befriedigender Ausbeute und Reinheit ge-#vonnen wird.
Process for the preparation of a new disubstituted nicotinic acid amide. The invention relates to a process for the preparation of a new disubstituted nicotinic acid amide of the formula
EMI0001.0007
ivelehes characterized. is that you can get a reactive ester of the alcohol of the formula
EMI0001.0014
With. one the rest
EMI0001.0016
the supplying connection.
The reactive ester of alcohol I can be, for example, a hydrogen halide, a sulfuric acid, an alkyl or arylsulfonic acid ester. Instead of the free amino alcohol ester, a salt of such can also be reacted.
It is advantageous to use an N-metal derivative of the amide corresponding to 1I as the compound supplying the radical 1I. However, the free amide II can also be reacted with a reactive amino alcohol ester with the aid of a metal amide as a condensing agent.
The nicotinic acid-N- (1,2-diphenyl-ethyl) -N - (ss-2; 6-dimethyl-piperidino-ethyl) -amide obtained in this way dissolves well in dilute acids, little in water and Petroleum ether. The new compound is said to be used as an antispasmodic and as an intermediate. find use for the production of further derivatives.
Example: 15.1 g of nicotinic acid-N- (1,2-diphenyl-ethyl) - amide, suspended in 150 em3 absol. Benzene, 2.3 g of powdered sodium amide are added and the mixture is heated to boiling temperature for a short time, during which time a strong evolution of ammonia occurs.
After the evolution of gas has subsided, 9.6 g of ss-2,6-dimethyl-piperidino-ethyl chloride, dissolved in 150 cms absolute. Benzene, add dropwise and then stir under reflux for a further 10 hours. After cooling, the solution is decanted from the excess sodium amide and extracted with 60% warm 1.5N hydrochloric acid until the extract reacts with a weakly acidic reaction.
The still warm hydrochloric acid extract is with. Charcoal filtered with lye. alkalized, exhausted with ether and the Alther distilled off. The residue is distilled in a high vacuum, the nicotinic acid e-N- (1,2-diphenyl-ethy 1) -N- (ss-2,6-dimethyl-piperidino-ethyl) -amide being obtained in good yield.
Instead of sodium amide as a condensation agent, nicotinic acid-N- (1,2-diphenyl-'ethyl) amide can be treated with sodium and the resulting sodium salt then with ss-2,6-dimethi-l-piperidino-ethy I chloride condense, whereby the lead compound is obtained in a satisfactory yield and purity.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294511T | 1951-03-01 | ||
| CH297726T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297726A true CH297726A (en) | 1954-03-31 |
Family
ID=25733487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297726D CH297726A (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) | CH297726A (en) |
-
1951
- 1951-03-01 CH CH297726D patent/CH297726A/en unknown
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