CH314211A - Process for the preparation of a quaternary ammonium salt - Google Patents
Process for the preparation of a quaternary ammonium saltInfo
- Publication number
- CH314211A CH314211A CH314211DA CH314211A CH 314211 A CH314211 A CH 314211A CH 314211D A CH314211D A CH 314211DA CH 314211 A CH314211 A CH 314211A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- ammonium salt
- preparation
- compound
- methyl iodide
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines quaternären Ammoniumsalzes Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten Phenylaeetamid abgelei- teten quaternären Ammoniumsalzes, das da durch gekennzeichnet ist, dass eine Verbin dung der Formel
EMI0001.0010
mit Methyljodid 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 hydrolytische Umsetzung gewonnen werden.
<I>Beispiel</I> 22 g a;a-Diphenyl-b-piperidino-valeronitril wurden mit 140 m1 konzentrierter Schwefel säure und 14 mal Wasser während 4 Stunden auf eine Innentemperatur von 95 C auf dem Wasserbad erhitzt. Die Reaktionsmischung wurde hierauf auf Eis gegossen und mit Am moniumhydroxyd neutralisiert. Das entstan dene Öl wurde aus Äthylacetat kristallisiert und aus Isopropanol umkristallisiert.
8,5 g a;a-Diphenyl-8-piperidino-valeronitril (Smp.119-120 C) wurden. in 150 ml Äthanol in einer Druckflasche gelöst, 10g Methyljodid zugegeben und die Mischung auf dem Wasser- bad während 3 Stunden erwärmt.
Die Kristalle, die sich beim Abkühlen bildeten, wurden aus Methanol umkristallisiert. Das erhaltene qua- ternäre Jodid zeigte einen Schmelzpunkt von 218-219 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 acetamide and which is characterized in that a compound of the formula
EMI0001.0010
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 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> 22 g of a; a-diphenyl-b-piperidino-valeronitrile were heated with 140 ml of concentrated sulfuric acid and 14 times water for 4 hours to an internal temperature of 95 C on a water bath. The reaction mixture was then poured onto ice and neutralized with ammonium hydroxide. The resulting oil was crystallized from ethyl acetate and recrystallized from isopropanol.
8.5 g of a; a-diphenyl-8-piperidino-valeronitrile (m.p. 119-120 C) were. Dissolve in 150 ml of ethanol in a pressure bottle, add 10 g of methyl iodide and heat the mixture on a water bath for 3 hours.
The crystals that formed on cooling were recrystallized from methanol. The quaternary iodide obtained had a melting point of 218-219 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314211XA | 1949-11-07 | 1949-11-07 | |
| CH307790T | 1950-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314211A true CH314211A (en) | 1956-05-31 |
Family
ID=25735320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314211D CH314211A (en) | 1949-11-07 | 1950-11-07 | Process for the preparation of a quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314211A (en) |
-
1950
- 1950-11-07 CH CH314211D patent/CH314211A/en unknown
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