CH314212A - Process for the preparation of a quaternary ammonium salt - Google Patents
Process for the preparation of a quaternary ammonium saltInfo
- Publication number
- CH314212A CH314212A CH314212DA CH314212A CH 314212 A CH314212 A CH 314212A CH 314212D A CH314212D A CH 314212DA CH 314212 A CH314212 A CH 314212A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- ammonium salt
- preparation
- compound
- methyl iodide
- Prior art date
Links
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines quaternären Ammoniumsalzes Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten Phenylacetamid abgelei- teten quaternären Ammoniumsalzes, das da durch gekennzeichnet ist, dass eine Verbin dung der Formel
EMI0001.0007
mit 1Tethyljodid umgesetzt wird. Die so her gestellte Verbindung soll zu pharmazeutischen Zwecken Verwendung finden.
Die antispasmodische Wirkung des so er haltenen quaternären Ammoniumsalzes ist derjenigen der freien Base erheblich über legen. Im weiteren kommt dem Salz auch eine mydriatische Wirksamkeit zu.
Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspre- ehenden Nitril durch hydrolytisehe Umsetzung gewonnen werden.
<I>Beispiel</I> 33 g a,a-Diphenyl-a-piperidino-hexansäure- nitril wurden mit 1.10 ml konzentrierter Schwefelsäure und l.4 ml Wasser während 4 Stunden auf eine Innentemperatur von 95 C auf dem Wasserbad erhitzt. Die Reaktions- misehung wurde hierauf auf Eis gegossen und mit. Ammoniumhydroxyd neutralisiert. Das entstandene Öl wurde aus Äthylacetat kristal lisiert und aus Isopropanol umkristallisiert.
9 g a,a-Diphenyl-a-piperidino.-hexansäure- amid (Smp. 89-90 C) wurden in 150 ml Athanol in einer Druckflasche gelöst, 10 g Methyljodid zugegeben und die Mischung wäh rend 3 Stunden auf dem Wasserbad erhitzt. Die sich beim Abkühlen bildenden Kristalle wurden aus Methanol umkristallisiert. Das erhaltene quaternäre Jodid zeigte. einen Smp. von 147-1490 C.
Process for the preparation of a quaternary ammonium salt The present invention relates to a process for the preparation of a new quaternary ammonium salt derived from a substituted phenylacetamide, which is characterized in that a compound of the formula
EMI0001.0007
is reacted with 1-methyl iodide. The compound thus established is intended to 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.
<I> Example </I> 33 g of a, a-diphenyl-a-piperidino-hexanoic acid nitrile were heated with 1.10 ml of concentrated sulfuric acid and 1.4 ml of water to an internal temperature of 95 C on a water bath for 4 hours. The reaction mixture was then poured onto ice and mixed with. Ammonium hydroxide neutralized. The resulting oil was crystallized from ethyl acetate and recrystallized from isopropanol.
9 g of a, a-diphenyl-a-piperidino.-hexanoic acid amide (melting point 89-90 ° C.) were dissolved in 150 ml of ethanol in a pressure bottle, 10 g of methyl iodide were added and the mixture was heated on a water bath for 3 hours. The crystals which formed on cooling were recrystallized from methanol. The quaternary iodide obtained showed. a m.p. of 147-1490 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314212XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314212A true CH314212A (en) | 1956-05-31 |
Family
ID=25735321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314212D CH314212A (en) | 1949-11-07 | 1950-11-07 | Process for the preparation of a quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314212A (en) |
-
1950
- 1950-11-07 CH CH314212D patent/CH314212A/en unknown
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