CH301676A - 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
- CH301676A CH301676A CH301676DA CH301676A CH 301676 A CH301676 A CH 301676A CH 301676D A CH301676D A CH 301676DA CH 301676 A CH301676 A CH 301676A
- Authority
- CH
- Switzerland
- Prior art keywords
- nicotinic acid
- acid amide
- preparation
- new
- formula
- Prior art date
Links
- 238000000034 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
- 238000002360 preparation method Methods 0.000 title description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- -1 di-substituted nicotinic acid amide Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 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
- 238000004519 manufacturing process Methods 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
- 230000002921 anti-spasmodic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- 239000003921 oil Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 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
- 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. (Tegenstand der Erfindung ist ein Verfah ren zur Herstellung eines neuen disubstituier- ten Nicotinsäureamids der Formel
EMI0001.0009
welches dadurch gekennzeichnet ist, dass man einen reaktionsfähigen Ester des Alkohols der Formel
EMI0001.0010
mit einer den Rest
EMI0001.0011
abgebenden Verbindung umsetzt.
Als den Rest II abgebende Verbindungen kommen insbesondere das Dimethylamin 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-äthy1)-N- (3'-dimethylamino -propyl) ] - amid bildet ein nahezu farbloses Öl, welches unter 0,05 mm bei 215-225 siedet und sich gut in verdünnten Säuren, wenig in Wasser und Petroläther löst. Das Chlorhydrat schmilzt aus 11lethylisobutylketon umkristallisiert bei 7 0-80 und ist amorph. Die neue Verbindung soll als Spasmolytikim und als Zwischenpro dukt zur Herstellung weiterer Derivate Ver wendung finden.
<I>Beispiel:</I> 37,9g N-(y-Chlor-propyl)-N-(1,2-diphenyl- äthyl)-nicotinsäureamid werden mit 5,5g Di- inethyjamin und 100 cm3 Benzol im Autokla- ven 5 Stunden bei 100 geschüttelt. Anschlie ssend dampft man zur Trockne ein, verrührt mit. 2n-Natronlauge und nimmt das sich ab scheidende Öl in Chloroform auf, trocknet, verdampft und destilliert den Rückstand im Hochvakuum.
Man erhält so das unter 0,05 mm bei 215 bs 225 siedende Nicotinsäure-[N-(1,2-diphe- nyl-äthyl) -N- (3'-dimethylamino-propyl) ] -amid in guter Ausbeute als fast farbloses Öl. Das Chlorhydrat der Base schmilzt aus Methyliso- butyllketon umkristallisiert bei 70-80 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
EMI0001.0009
which is characterized in that one has a reactive ester of the alcohol of the formula
EMI0001.0010
with one the rest
EMI0001.0011
transferring connection.
Particularly suitable compounds which donate the radical II are dimethylamine itself and its N-metal derivatives.
The reactive esters of alcohol I that can be used are, 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-ethy1) -N- (3'-dimethylamino-propyl)] amide obtained in this way forms an almost colorless oil, which boils below 0.05 mm at 215-225 and dissolves well in dilute acids, little in water and petroleum ether. The chlorohydrate melts from 11lethylisobutylketon recrystallized at 70-80 and is amorphous. The new compound is said to be used as a spasmolytic agent and as an intermediate product for the manufacture of further derivatives.
<I> Example: </I> 37.9 g of N- (y-chloro-propyl) -N- (1,2-diphenyl-ethyl) -nicotinic acid amide are mixed with 5.5 g of di-methylamine and 100 cm3 of benzene in the car ven shaken at 100 for 5 hours. It is then evaporated to dryness and stirred with. 2N sodium hydroxide solution and the oil which separates is taken up in chloroform, dried, evaporated and the residue is distilled in a high vacuum.
The nicotinic acid [N- (1,2-diphenyl-ethyl) -N- (3'-dimethylamino-propyl)] -amide boiling below 0.05 mm at 215 to 225 is obtained in good yield as an almost colorless one Oil. The hydrochloride of the base melts from methyl isobutyl ketone, recrystallizes at 70-80 and is amorphous.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294511T | 1951-03-01 | ||
| CH301676T | 1951-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301676A true CH301676A (en) | 1954-09-15 |
Family
ID=25733492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301676D CH301676A (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) | CH301676A (en) |
-
1951
- 1951-04-03 CH CH301676D patent/CH301676A/en unknown
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