CH297721A - 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
- CH297721A CH297721A CH297721DA CH297721A CH 297721 A CH297721 A CH 297721A CH 297721D A CH297721D A CH 297721DA CH 297721 A CH297721 A CH 297721A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- amide
- preparation
- nicotinic acid
- acid amide
- 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)
Description
Verfahren zur Herstellung eines neuen disubstituierten Nicotinsäureamids. Gegenstand der Erfindung ist ein Ver- Fal7ren zur Herstellung eines neuen disubsti- tllierten Nieotinsäureamids der Formel
EMI0001.0010
@celd@es dadurch gekeniizeiehnet ist,
dass man einen reaktionsfähi-en Ester des Alkohols der Foren el
EMI0001.0019
mit einer den Rest
EMI0001.0020
liefernden Verbindung umsetzt.
Ms reaktionsfähige Ester des Alkohols I kann man beispielsweise einen Halogenwasser stoffsäure-, einen Schwefelsäure-, einen: Alkyl- bz #, .1i;
vlsulfonsä.iireester verwenden, Statt (]es freien Aminoalkoholesterskann , auch ein alz eines solchen zur Reaktion gebraeht wer- (len. Vorteilhaft verwendet man als den Rest II liefernde Verbindung ein N-Metallderivat des II 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 Nicotinsäure-N-(1,2-di- phenyl-äth5-1)-N-('?'-piperidino-äthyl)-amid bil det ein leicht, gelblich gefärbtes Öl, welches unter 0,08 mm hei \?50-2'60 C siedet. und sich gut in verdünnten. Säuren, wenig in Wasser und Petrolä.ther löst.
Die neue Ver bindung soll als Spasmolytikum und als Zwi- sehenprodukt zur Herstellung weiterer Deri vate Verwendung finden.
<I>Beispiel.:</I> 30g Nieotinsäure-N-(1,'?-diphenyl-äthy1)- amid, suspendiert in 300 ems absolutem Ben zol, werden mit. 4;6 g gepulvertem Natrium- ainid versetzt. und kurze Zeit auf Siedetem peratur erhitzt, wobei eine starke Ammoniak entwicklung eintritt.
Nachdem die Gasent wicklung nachgelassen hat, lässt man 16,6 P Piperidino-äthylchlorid, gelöst in 300 cm3 ab solutem Benzol, zutropfen und rührt dann weitere 7 Stunden unter Rüekflusskochen.. Nach dem Erkalten wird die Lösung vom überschüssigen Natrium amid abdekantiert und mit. 60 C warmer 1,5n-Salzsäure ausgezogen, bis der Auszug sehwach sauer reagiert.
Der noch warme salzsaure Auszug wird mit Kohle filtriert, alkalisiert. und erschöpfend aus,--e- äthert. Nach dem Trocknen über Natriumsul fat wird der Äther abdestilliert und der Rück stand im Hochvakuum destilliert, wobei man 32,9 g des unter 0,08 mm bei 250-260 sie denden Nieotinsä.ure-N-(1,2-diphenyl - äthyl)- N-(2'-piperidino-äthyl.)-amids als gelbliches<B>01</B> in einer Ausbeute von 55 !o gewinnt.
An Stelle von Natriumamid als Kondensa- tionsmittel kann man das NieotinsäLire-N- (1,2-diphenyl-äthyl)-amid mit Natrium be handeln und das entstandene Natriumsalz an schliessend mit Piperidino-äthylehlorid kon- den>sieren, wobei die gleiche Verbiindun- in befriedigender Ausbeute und Reinheit gewon nen, wird.
Process for the preparation of a new disubstituted nicotinic acid amide. The invention relates to a process for the production of a new disubstituted Nieotinsäureamids of the formula
EMI0001.0010
@ celd @ it is thereby marked,
that a reactive ester of the alcohol of the forum el
EMI0001.0019
with one the rest
EMI0001.0020
the supplying connection.
Ms reactive ester of alcohol I can be, for example, a hydrogen halide, a sulfuric acid, an: alkyl bz #, .1i;
Use a sulfonic acid ester, instead of a free amino alcohol ester, a salt of one of these can also be used for the reaction. An N-metal derivative of the amide corresponding to II is advantageously used as the compound which provides the radical II free amide,
II with the aid of a metal amide as a condensing agent to react with a reactive amino alcohol ester, the nicotinic acid N- (1,2-diphenyl-eth5-1) -N - ('?' - piperidino-ethyl) -amide obtained bil det a light, yellowish colored oil, which boils below 0.08 mm hot \? 50-2'60 C. and well diluted in. Acids, dissolves little in water and petroleum ether.
The new connection is intended to be used as an antispasmodic and as an intermediate product for the manufacture of further derivatives.
<I> Example .: </I> 30g of nieotinic acid-N- (1, '? - diphenyl-ethy1) - amide, suspended in 300 ems of absolute benzene, are mixed with. 4; 6 g of powdered sodium ainide added. and heated to boiling temperature for a short time, during which a strong ammonia development occurs.
After the development of gas has subsided, 16.6 P piperidino-ethyl chloride, dissolved in 300 cm3 of absolute benzene, is added dropwise and then stirred for a further 7 hours under reflux. After cooling, the solution is decanted from the excess sodium amide and mixed with it. 1.5N hydrochloric acid at 60 C until the extract reacts weakly acidic.
The still warm hydrochloric acid extract is filtered with charcoal and alkalized. and exhaustively from, - ethereal. After drying over sodium sulfate, the ether is distilled off and the residue is distilled in a high vacuum, 32.9 g of Nieotinsä.ure-N- (1,2-diphenyl - ethyl which ends below 0.08 mm at 250-260) ) - N- (2'-piperidino-ethyl.) - amide wins as yellowish <B> 01 </B> in a yield of 55%.
Instead of sodium amide as a condensing agent, the NieotinsäLire-N- (1,2-diphenyl-ethyl) -amide can be treated with sodium and the resulting sodium salt can then be condensed with piperidino-ethyl chloride, the same compound - Won in a satisfactory yield and purity, is.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294511T | 1951-03-01 | ||
| CH297721T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297721A true CH297721A (en) | 1954-03-31 |
Family
ID=25733482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297721D CH297721A (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) | CH297721A (en) |
-
1951
- 1951-03-01 CH CH297721D patent/CH297721A/en unknown
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