CH314214A - Process for the preparation of a quaternary ammonium salt - Google Patents
Process for the preparation of a quaternary ammonium saltInfo
- Publication number
- CH314214A CH314214A CH314214DA CH314214A CH 314214 A CH314214 A CH 314214A CH 314214D A CH314214D A CH 314214DA CH 314214 A CH314214 A CH 314214A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- ammonium salt
- preparation
- methyl
- compound
- 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N Ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 230000000875 corresponding Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical group [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002911 mydriatic Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Description
Verfahren zur Herstellung: eines quaternären Ammoniumsalzes Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten Phenyla,eetamid abgelei- teten quaternären Ammoniumsalzes, das da durch gekennzeichnet ist, dass eine Verbin dung der Formel
EMI0001.0013
mit Methyljodid umgesetzt wird.
Die so her gestellte Verbindung soll zu pharmazeutischen Zwecken Verwendung finden.
Die antispasmodische Wirkung des so erhaltenen 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 hydrolytische Umsetzung gewonnen werden.
Beispiel 32 g von a,a-Diphenyl-ss-methyl-y-piperidino- hutyronitril wurden mit 140 ml konzentrierter Schwefelsäure und 14 ml Wasser während 4 Stunden auf eine Innentemperatur von 95 C auf dem Wasserbad erhitzt.
Die Reaktions- mischumg wurde hierauf auf Eis gegossen und mit Ammoniumhydroxyd neutralisiert. Das erhaltene Öl wurde aus Äthylacetat kristall i- siert und aus Isopropanol umkristallisiert.
8,5 g a,a-Diphenyl-fl-methyl-y-piperidino- butyramid (Smp. 155-157 C) wurden in 150 ml Äthanol in einer Druckflasche gelöst, 10 g Methyljodid zugegeben und die Mischung während 3 Stunden auf dem Wasserbad er hitzt. Die beim Abkühlen sich bildenden Kri stalle wurden umkristallisiert; das erhaltene quaternäre Jodid zeigte einen Smp. von 105 bis 106 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 which is derived from a substituted phenyl, etamide and which is characterized in that a compound of the formula
EMI0001.0013
is reacted with methyl iodide.
The compound thus established 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. 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 32 g of α, α-diphenyl-ß-methyl-γ-piperidino-hutyronitrile were heated to an internal temperature of 95 ° C. on a water bath with 140 ml of concentrated sulfuric acid and 14 ml of water for 4 hours.
The reaction mixture was then poured onto ice and neutralized with ammonium hydroxide. The oil obtained was crystallized from ethyl acetate and recrystallized from isopropanol.
8.5 ga, α-diphenyl-fl-methyl-γ-piperidino-butyramide (melting point 155-157 ° C.) were dissolved in 150 ml of ethanol in a pressure bottle, 10 g of methyl iodide were added and the mixture was kept on a water bath for 3 hours heats. The crystals which formed on cooling were recrystallized; the quaternary iodide obtained had a melting point of 105 to 106 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314214XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314214A true CH314214A (en) | 1956-05-31 |
Family
ID=25735323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314214D CH314214A (en) | 1949-11-07 | 1950-11-07 | Process for the preparation of a quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314214A (en) |
-
1950
- 1950-11-07 CH CH314214D patent/CH314214A/en unknown
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