CH301677A - 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
- CH301677A CH301677A CH301677DA CH301677A CH 301677 A CH301677 A CH 301677A CH 301677D A CH301677D A CH 301677DA CH 301677 A CH301677 A CH 301677A
- Authority
- CH
- Switzerland
- Prior art keywords
- nicotinic acid
- preparation
- acid amide
- new
- formula
- 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
- -1 1,2-diphenyl-ethyl Chemical group 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 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 description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen disubstituierten Nicotinsäureamids. Gegenstand der Erfindung ist ein Verfah ren zur Herstellung eines neuen disubstit.uier- ten Nieotinsäureamids der Formel
EMI0001.0006
welches dadurch gekennzeichnet ist, dass man einen reaktionsfähigen Ester des Alkohols der Formel
EMI0001.0007
mit einer den Rest
EMI0001.0008
< < bgebenden Verbindung umsetzt.
Als den Rest II abgebende Verbindungen kommen insbesondere das Diäthylamin selbst und seine N-Metallderivate in Betracht.
Als reaktionsfähige Ester des Alkohols I kann man beispielsweise einen Halogenwasser stoffsäure-, einen Schwefelsäure-, einen Alkyl- bzw. Arylsulfonsäureester verwenden. Statt des freien Aminoalkoholesters (I) und des freien Amins (II) können auch ihre Salze zur Reaktion gebracht werden.
Die Umsetzung kann in An- oder Abwesen heit eines Lösungs- bzw. Verdünnungsmittels und eines Kondensationsmittels durchgeführt werden.
Das so erhaltene Nicotinsäure-[N-(1,2-di- phenyl - äthyl) -N - (3' - 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 schmilzt aus 1Vlethylisobutylketon umkristallisiert bei 50-70" und ist amorph.
Die neue Verbindung soll als Spasmolytikum und als Zwischenpro dukt zur Herstellung weiterer Derivate Ver wendung finden.
<I>Beispiel:</I> 37,9 g N-(y-Chlor-propyl)-N-(1,2-diphenyl- äthyl)-nicotinsäureamid werden mit 9 g Di- äthvlamin und 120 em3 Benzol im Autoklaven 4 Stunden bei 100 geschüttelt. Anschliessend dampft man zur Trockne ein, verrührt mit 2n-Natronlauge und nimmt das sich abschei- dende Öl in Chloroform auf, trocknet, ver dampft und destilliert den Rückstand im Hochvakuum.
Man erhält so das unter 0,15 mm bei 235 bis 240 siedende Nicotinsäure-[N-(1,2-diphe- nyl-äthyl)-N-(3'-diäthylamino-propyl) ]-amid in guter Ausbeute als fast farbloses Öl. Das Chlorhydrat der Base schmilzt aus Methvjiso- butylketon umkristallisiert bei 50-70 und ist amorph.
Process for the preparation of a new disubstituted nicotinic acid amide. The invention relates to a process for the preparation of a new disubstituted Nieotinsäureamids of the formula
EMI0001.0006
which is characterized in that one has a reactive ester of the alcohol of the formula
EMI0001.0007
with one the rest
EMI0001.0008
<<implements the source connection
Particularly suitable compounds which donate the remainder II are diethylamine itself and its N-metal derivatives.
The reactive ester of alcohol I can be, for example, a hydrogen halide, a sulfuric acid, an alkyl or aryl sulfonic acid ester. Instead of the free amino alcohol ester (I) and the free amine (II), their salts can also be reacted.
The reaction can be carried out in the presence or absence of a solvent or diluent and a condensing agent.
The nicotinic acid [N- (1,2-diphenyl - ethyl) - N - (3 '- diethylamino - propyl)] - amide thus obtained forms an almost colorless oil which boils below 0.15 mm at 235-240 and dissolves well in dilute acids, little in water and petroleum ether. The chlorohydrate melts from 1Vlethylisobutylketon recrystallized at 50-70 "and is amorphous.
The new compound is said to be used as an antispasmodic and as an intermediate product for the manufacture of other derivatives.
<I> Example: </I> 37.9 g of N- (γ-chloro-propyl) -N- (1,2-diphenyl- ethyl) -nicotinic acid amide are mixed with 9 g diethylamine and 120 em3 benzene in autoclave 4 Shaken at 100 hours. It is then evaporated to dryness, stirred with 2N sodium hydroxide solution and the oil which separates out is taken up in chloroform, dried, evaporated and the residue is distilled in a high vacuum.
Nicotinic acid- [N- (1,2-diphenyl-ethyl) -N- (3'-diethylamino-propyl)] -amide boiling below 0.15 mm at 235 to 240 is obtained in good yield as an almost colorless one Oil. The chlorohydrate of the base melts from Methvjisobutylketon recrystallized at 50-70 and is amorphous.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294511T | 1951-03-01 | ||
| CH301677T | 1951-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301677A true CH301677A (en) | 1954-09-15 |
Family
ID=25733493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301677D CH301677A (en) | 1951-03-01 | 1951-04-03 | Process for the preparation of a new disubstituted nicotinic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301677A (en) |
-
1951
- 1951-04-03 CH CH301677D patent/CH301677A/en unknown
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