CH314209A - Process for the preparation of a quaternary ammonium salt - Google Patents
Process for the preparation of a quaternary ammonium saltInfo
- Publication number
- CH314209A CH314209A CH314209DA CH314209A CH 314209 A CH314209 A CH 314209A CH 314209D A CH314209D A CH 314209DA CH 314209 A CH314209 A CH 314209A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- ammonium salt
- diphenyl
- quaternary ammonium
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000002911 mydriatic effect Effects 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines quaternären Ammoniumsalzes
Die vorliegende Erfindung betrifft ein Verfahren zur Herstell'ung eines neuen, von einem substituierten Phenylacetamid abgeleiteten quaternären Ammoniumsalzes, das dadureh gekennzeiehnet ist, dass man a Di- phenyl- ¯ -methyl-γ- dimethylamino-butyroamid mit Methyljodid umsetzt. Die so hergestellte Verbindung von der Formel
EMI1.1
li, einen Sehmelzpunkt von 204-205 C. Sie soll zu pharmazeutischen Zwecken Verwendung finden.
Die antispasmodische Wirkung des so erhaltenen quaternären Ammoniumsalzes ist derjenigen der freien Base erheblich überlegen. Im weiteren kommt dem Salz auch eine mydriatische Wirksamkeit zu.
Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspre chenden Nitril durch hydrolytische Umsetzung gewonnen werden.
Beispiel
30 g α,α-Diphenyl- ¯ -methyl-γ-dimethyl- amino-butyronitril wurden mit 140 ml konzen- trierter Schwefelsäure und 14 ml Wasser 4 Stunden lang auf dem Wasserbad auf 95 C erhitzt. Das Reaktionsgemisch wurde dann au, Eis gegossen und mit Ammoniak neutralisiert. Das sich hierbei abseheidende O1 wurde aus ¯thylacetat und hernach zweimal aus Iso- propylalkohol zur Kristallisation gebracht.
Das Produkt schmolz bei 151-152, 5 C.
8 g des erhaltenen α,α-Diphenyl- ¯ -methyl- y-dimethylamino-butyroamids wurden in 150 ml Äthanol gelost und in einen druckfesten Kol ben verbracht. Naeh Zugabe von 10 g Methyl jodid wurde die Mischung 3 Stunden lang aui dem Wasserbade erwärmt. Beim Abkühlen schieden sieh Kristalle aus, welche umkristal- lisiert einen Schmelzpunkt von 204-205 C aufwiesen. Die neue Verbindung hat die Formel
EMI1.2
PATENTANSPRUCH
Verfahren zur Herstellung eines quaternÏren. Ammoniumsalzes, dadureh gekennzeich-
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a quaternary ammonium salt
The present invention relates to a process for the production of a new quaternary ammonium salt derived from a substituted phenylacetamide, which is characterized in that a diphenyl-¯-methyl-γ-dimethylamino-butyroamide is reacted with methyl iodide. The compound so prepared of the formula
EMI1.1
li, a melting point of 204-205 C. It should be used for pharmaceutical purposes.
The antispasmodic effect of the quaternary ammonium salt thus obtained is considerably superior to that of the free base. The salt also has a mydriatic effect.
The base used as the starting product can be obtained in a known manner from the corresponding nitrile by hydrolytic conversion.
example
30 g of α, α-diphenyl- ¯ -methyl-γ-dimethylamino-butyronitrile were heated with 140 ml of concentrated sulfuric acid and 14 ml of water on a water bath at 95 ° C for 4 hours. The reaction mixture was then poured onto ice, and neutralized with ammonia. The O1 which separated out was crystallized from ethyl acetate and then twice from isopropyl alcohol.
The product melted at 151-152.5 C.
8 g of the α, α-diphenyl- ¯ -methyl-γ-dimethylamino-butyroamide obtained were dissolved in 150 ml of ethanol and placed in a pressure-tight flask. After adding 10 g of methyl iodide, the mixture was heated in the water bath for 3 hours. On cooling, crystals separated out which, when recrystallized, had a melting point of 204-205 ° C. The new compound has the formula
EMI1.2
PATENT CLAIM
Process for the production of a quaternary. Ammonium salt, dadureh marked
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314209XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314209A true CH314209A (en) | 1956-05-31 |
Family
ID=25735318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314209D CH314209A (en) | 1949-11-07 | 1949-11-07 | Process for the preparation of a quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314209A (en) |
-
1949
- 1949-11-07 CH CH314209D patent/CH314209A/en unknown
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