CH314207A - Process for the preparation of a quaternary ammonium base - Google Patents
Process for the preparation of a quaternary ammonium baseInfo
- Publication number
- CH314207A CH314207A CH314207DA CH314207A CH 314207 A CH314207 A CH 314207A CH 314207D A CH314207D A CH 314207DA CH 314207 A CH314207 A CH 314207A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- preparation
- ammonium base
- recrystallized
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- 229950001902 dimevamide Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer quaternären Ammoniumbase
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung einer neuen, von einem substituierten Phenylaeetamid abgeleiteten quaternären Ammoniumbase, das dadurch gekennzeichnet ist, dass man das y Dimethylamino-a, a-diphenylvaleroamid mit Äthyljodid umsetzt. Die so hergestellte Ver bindlmg der Formel
EMI1.1
sehmilzt, aus Methanol umkristallisiert, bei 192-192, 5 C. Sie soll zu pharmazeutischen Zwecken Verwendung finden.
Die ant. ispasmodisehe Wirkung des so erhaltenen qua. ternären Ammoniumsalzes ist derjenigen der freien Base iiberlegen. Im weiteren kommt dem Salz auch eine mydriatisehe Wirksamkeit Zll.
Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspre- ehenden Nitril durch hyd'rolytisehe Umsetzung gewonnenwerden.
Beispiel
Eine Mischung von 14 g (0,05 Mol) a, a Diphenyl-y-dimethyla. mino-valeronit. ril, 16 g (0,2 Mol) Natriumacetat, 14 g (0,2 Mol) lTydroxylamin-hydroehlorid und 75 ml sthyl- alkohol wurde am Rückfluss 18 Stunden lang gekocht und dann abgekühlt, in Wasser gegossen und mit Ammoniak neutralisiert. Das hierbei durch Hydrolyse des Nitrils entstan- dene Säureamid wurde zur Reinigung drei Mal aus Isopropylalkohol umkristallisiert. Es hatte hierauf einen Smp. von 177-179"C.
Die gleiche Verbindung lässt sich auch herstellen durch Hydrolyse des Val. eronitrils mit 92 /oiger Sehwefelsäure durch zweistün- diges Erwärmen auf dem Wasserbad, Abkühlen und Eingiessen in Eis.
8 g des erhaltenen y-Dimethyl-a, a-diphenyl- valeroamids wurden in 150 ml Äthanol gelöst und in einen druckfesten Kolben verbracht.
Naeh Zugabe von 12 g Äthyljodid wurde die Mischung 3 Stunden lang auf dem Wasserbade erwärmt. Beim Abkühlen schieden sich Kristalle aus, welche drei Mal aus Methanol umkristallisiert wurden und hierauf einen Schmelzpunkt von 19192, 5 C aufwiesen.
Die neue Verbindung hat die Formel
EMI2.1
Process for the preparation of a quaternary ammonium base
The present invention relates to a process for the preparation of a new quaternary ammonium base derived from a substituted phenyl acetamide, which is characterized in that the γ-dimethylamino-α, α-diphenylvaleroamide is reacted with ethyl iodide. The compound of the formula thus produced
EMI1.1
sehmelzt, recrystallized from methanol, at 192-192.5 C. It is said to be used for pharmaceutical purposes.
The ant. ispasmodic effect of the thus obtained qua. ternary ammonium salt is superior to that of the free base. In addition, 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 hydrolysis.
example
A mixture of 14 g (0.05 mol) of a, a Diphenyl-γ-dimethyla. mino-valeronite. ril, 16 g (0.2 mol) of sodium acetate, 14 g (0.2 mol) of hydroxylamine hydrochloride and 75 ml of ethyl alcohol were refluxed for 18 hours and then cooled, poured into water and neutralized with ammonia. The acid amide formed by hydrolysis of the nitrile was recrystallized three times from isopropyl alcohol for purification. It then had a m.p. of 177-179 "C.
The same compound can also be produced by hydrolysis of the val. Eronitrile with 92% sulfuric acid by heating for two hours on a water bath, cooling and pouring into ice.
8 g of the obtained γ-dimethyl-a, a-diphenylvaleroamide were dissolved in 150 ml of ethanol and placed in a pressure-tight flask.
After adding 12 g of ethyl iodide, the mixture was heated on the water bath for 3 hours. On cooling, crystals separated out, which were recrystallized three times from methanol and then had a melting point of 19192.5 ° C.
The new compound has the formula
EMI2.1
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314207XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314207A true CH314207A (en) | 1956-05-31 |
Family
ID=25735316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314207D CH314207A (en) | 1949-11-07 | 1950-11-07 | Process for the preparation of a quaternary ammonium base |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314207A (en) |
-
1950
- 1950-11-07 CH CH314207D patent/CH314207A/en unknown
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