CH314213A - Process for the preparation of a quaternary ammonium salt - Google Patents
Process for the preparation of a quaternary ammonium saltInfo
- Publication number
- CH314213A CH314213A CH314213DA CH314213A CH 314213 A CH314213 A CH 314213A CH 314213D A CH314213D A CH 314213DA CH 314213 A CH314213 A CH 314213A
- Authority
- CH
- Switzerland
- Prior art keywords
- ammonium salt
- quaternary ammonium
- preparation
- production
- piperidino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229950001902 dimevamide Drugs 0.000 description 1
- 230000000694 effects Effects 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 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)
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., da.ss eine Verbin dung der Formel
EMI0001.0009
mit. lIethyljodid umgesetzt wird. Die so her- @estellte Verbindung soll zu pharmazeutischen Zwecken Verwendung finden.
Die antispasmodische Wirkung des so er haltenen quaternären Ammoniumsalzes ist derjenigen der freien Base erheblich Übpr- leo-en. Im weiteren kommt dem Salz auch eine niy(Iriatische Wirksamkeit zu.
Die als Ausgangsprodukt verwende Base kann in bekannter Weise aus dem entsi)r @-- clienden Nitril durch hydrolytische Umsetzung gewonnen werden.
<I>Beispiel</I> 32 g a,a-Diphenyl-y-piperidino-valeronitril wurden mit 140 ml konzentrierter Sehwefel- säure und 14 ml Wasser während 4 Stunden auf eine Innentemperatur von 95 C auf dein Wasserbad erhitzt. Die ReaktionsmischuneT wurde hierauf auf Eis gegossen und mit Am moniumhydroxyd neutralisiert.
Das erhaltene Öl kristallisierte aus Äthylacetat, worauf eine zweite Kristallisation aus Isopropanol erfolgte: 8,5 g a,a-Diphenyl-y-piperidino-valeramid (Smp. 158,5-160 C) wurden in 150 ml Äthanol in einer Druekflasche gelöst,
10 g Methyljodid zugegeben und die Mischung wäh rend 3 Stunden auf dem MTasserbad erwärmt. Die sich bei der Abkühlung ausseheidenden Kristalle wurden dreimal aus Methanol um- kristallisiert.
Das erhaltene quaternäre Jodid zeigte einen Smp. von 201-202 C.
Process for the production 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 by being a compound of the formula
EMI0001.0009
With. LIethyliodid is implemented. The connection established in this way is intended to be used for pharmaceutical purposes.
The antispasmodic effect of the quaternary ammonium salt obtained in this way is considerably superior to that of the free base. Furthermore, the salt also has a niy (Iriatic effect.
The base used as the starting product can be obtained in a known manner from the desirinating nitrile by hydrolytic conversion.
<I> Example </I> 32 g of α, α-diphenyl-γ-piperidino-valeronitrile were heated with 140 ml of concentrated sulfuric acid and 14 ml of water to an internal temperature of 95 ° C. in the water bath for 4 hours. The reaction mixture was then poured onto ice and neutralized with ammonium hydroxide.
The oil obtained crystallized from ethyl acetate, whereupon a second crystallization from isopropanol took place: 8.5 g of a, a-diphenyl-y-piperidino-valeramide (melting point 158.5-160 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 the M water bath for 3 hours. The crystals which separated out on cooling were recrystallized three times from methanol.
The quaternary iodide obtained had a melting point of 201-202 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314213XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314213A true CH314213A (en) | 1956-05-31 |
Family
ID=25735322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314213D CH314213A (en) | 1949-11-07 | 1950-11-07 | Process for the preparation of a quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314213A (en) |
-
1950
- 1950-11-07 CH CH314213D patent/CH314213A/en unknown
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