CH297715A - 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
- CH297715A CH297715A CH297715DA CH297715A CH 297715 A CH297715 A CH 297715A CH 297715D A CH297715D A CH 297715DA CH 297715 A CH297715 A CH 297715A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- nicotinic acid
- acid amide
- new
- compound
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 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
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001408 amides 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 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 2
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 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
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt 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
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen disubstituierten Nicotinsäureamids. Gegenstand der Erfindung ist ein Verfahren zur Herstellung eines netten disubsti- tuierten Nicotinsätireamids der Formel
EMI0001.0008
welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0010
deearboxy liert.
Die Decarboxylierung kann durch Er hitzen in An- oder Abwesenheit eines Lö- Srtn01s- 1)7w. erfolgen.
Die Verbindung der Formel. 1 kann bei spielsweise (Inreh Umsetzung von Chinolin- säureanhydrid mit N-(1;@D.iphenyl-äthyl) (:@'-methvl-N'-n-but@#1-aminoäthyl)-amin ge wonnen werden..
Es ist auch möglich, die ge bildete Verbindung der Formel I ohne Isolie rung zu deearboxylieren. Das so erhaltene Nicotinsäure-N-(1,2-di- phenyl-ät.h@,l) -N- (1V'-methyl-N'-n-but.yl-amino- äthyl)-amid löst sich gut. in verdünnten. Säu ren, wenig in Nasser und Petrolät.her.
Die neue Verbindung soll als Spasmolyti- kum und als Zwischenprodukt zur Herstel lung weiterer Derivate Verwendung finden. <I>Beispiel:</I> Zu 31,6 g geschmolzenem Chinolinsäurean- hydrid werden innert.
10 Minuten 31,0g N- (1,2-Diphenv 1-äthvl ) -N- ( @,T'-methpl-N'-n-butv'1- aminoäthvl)-amin zugetropft, wobei die T em- peratur um etwa 30 steigt. Anschliessend er hitzt man<B>15</B> -Minuten auf 1-60 und lässt dar nach die Schmelze erkalten. Die glasig er starrte lasse wird in 2n-Salzsäure gelöst, mit Natronlauge versetzt und mit.
Chloroform ex trahiert. Das Chloroform wird nach dem Trocknen über Natriumsulfat verdampft. Darauf löst man den Rückstand - einen schwarzen, dicken Sirup - in Äther, behan delt mit. Kohle und filtriert. Das Filtrat. wird mit 2n-Salzsäure ausgezogen und der salzsaure Auszug ebenfalls mit Kohle behandelt, fil- triert, nieder alkalisch gemacht und erschöp fend ausgeäthert. Nach dem Verdampfen des Äthers und Destillieren des Rückstandes im Hochvakuum gewinnt man das Nicotinsäure- N-(1,
2-diphenyl- äthy-1)-N- (N'-methvl-N'-n-bu- tvl-aminoäthyl)-amid in befriedigender Aus beute.
Die nette Verbindung löst sieh leicht in verdünnten Säuren, weni-er gut. in Wasser und Pet.roläther.
Process for the preparation of a new disubstituted nicotinic acid amide. The invention relates to a process for the preparation of a nice disubstituted nicotinic amide of the formula
EMI0001.0008
which is characterized in that the compound of the formula
EMI0001.0010
deearboxy liert.
The decarboxylation can be carried out by heating in the presence or absence of a solvent. Srtn01s- 1) 7w. respectively.
The compound of the formula. 1 can be obtained for example (Inreh conversion of quinolinic anhydride with N- (1; @ D.iphenyl-ethyl) (: @ '- methvl-N'-n-but @ # 1-aminoethyl) amine ..
It is also possible to deearboxylate the compound of formula I formed without isolation. The nicotinic acid-N- (1,2-diphenyl-ät.h @, l) -N- (1V'-methyl-N'-n-but.yl-amino-ethyl) -amide thus obtained dissolves well . in dilute. Acid, little in water and petroleum ether.
The new compound is said to be used as an antispasmodic and as an intermediate for the production of further derivatives. <I> Example: </I> To 31.6 g of melted quinolinic anhydride are inert.
10 minutes 31.0 g of N- (1,2-Diphenv 1-ethhvl) -N- (@, T'-methpl-N'-n-butv'1-aminoäthvl) amine was added dropwise, the temperature around about 30 rises. Then it is heated for <B> 15 </B> minutes to 1-60 and then allowed to cool down the melt. The glassy he stared is dissolved in 2N hydrochloric acid, mixed with sodium hydroxide and with.
Chloroform extracted. The chloroform is evaporated after drying over sodium sulphate. The residue - a thick black syrup - is then dissolved in ether, treated with. Charcoal and filtered. The filtrate. is extracted with 2N hydrochloric acid and the hydrochloric acid extract is also treated with charcoal, filtered, rendered low alkaline and etherified to exhaustion. After evaporation of the ether and distillation of the residue in a high vacuum, the nicotinic acid N- (1,
2-diphenyl-ethy-1) -N- (N'-methvl-N'-n-buttvl-aminoethyl) amide in a satisfactory yield.
The nice compound dissolves easily in dilute acids, less well. in water and petroleum ether.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297715T | 1951-03-01 | ||
| CH293815T | 1951-03-01 | ||
| CH297720T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297715A true CH297715A (en) | 1954-03-31 |
Family
ID=27178192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297715D CH297715A (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) | CH297715A (en) |
-
1951
- 1951-03-01 CH CH297715D patent/CH297715A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT200578B (en) | Process for the preparation of new N-aminoalkyl derivatives of azepines | |
| CH297715A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297716A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297714A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297710A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297718A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297712A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| DE826133C (en) | Process for the preparation of dihydroresorcinol carbamic acid esters | |
| CH297711A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297717A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH297708A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH496714A (en) | Process for the preparation of derivatives of 1,3,4,5-tetrahydrobenzodiazepine | |
| AT204558B (en) | Process for the preparation of new heterocyclic compounds | |
| CH297713A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| AT278787B (en) | PROCESS FOR THE PRODUCTION OF NEW CARBONIC ACIDS AND THEIR SALTS | |
| DE663375C (en) | Process for the preparation of nitrogen-containing condensation products | |
| AT272347B (en) | Process for the preparation of new pyridyl-dihydroisoquinolines and their acid addition salts | |
| DE2016084C3 (en) | Process for the preparation of 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one | |
| AT275518B (en) | Process for the preparation of new 1- (4-oxo-4-phenyl-butyl) -piperidines substituted in the 4-position and of their acid addition salts | |
| AT206424B (en) | Process for the preparation of the new bis-γ-chloropropyl) amine and its salts | |
| CH293815A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| DE944729C (en) | Process for the preparation of bacteriostatically active compounds | |
| AT238174B (en) | Process for the preparation of N- (2,3-dimethylphenyl) anthranilic acid and its salts | |
| AT281041B (en) | Process for the preparation of new piperazine compounds and their acid addition salts | |
| DE812314C (en) | Process for the preparation of 1,2-iminocyclohexanes |