CH297736A - Process for the preparation of a new quaternary salt. - Google Patents
Process for the preparation of a new quaternary salt.Info
- Publication number
- CH297736A CH297736A CH297736DA CH297736A CH 297736 A CH297736 A CH 297736A CH 297736D A CH297736D A CH 297736DA CH 297736 A CH297736 A CH 297736A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- quaternary salt
- new quaternary
- formula
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003839 salts Chemical group 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- -1 1,2-diphenyl-ethyl Chemical group 0.000 claims 1
- 230000002921 anti-spasmodic effect Effects 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen quaternären Salzes. Gegenstand der Erfindung ist ein Verfahren zur Herstellung eines neuen quaternären Salzes der Formel
EMI0001.0005
welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0006
mit hlethansulfonsäuremethylester quaterni- siert.
Der Umsatz geschieht vorzugsweise in An- wesenheit eines Lösungs- bzw. Verdünnungs mittels.
Bei Verwendung von 1 Mol Methansulfon- s ', ihn -e-niethylester auf 1 Mol der Verbindung I wurde die Beobachtung gemacht, dass das ter tiäre Stickstoffatom der Seitenkette vor dem Stickstoffatom des Pyridinringes quaternisiert wird.
Es ist wichtig, dass man nicht mit einem zu grossen Überschuss an Methansulfonsäure- methylester arbeitet, da sonst die Gefahr be steht., dass das Pyridinstickstoffatom auch qua- ternisiert wird. Das so erhaltene Nicotinsäure -(1,2-diphenyl-ätlryl)-1-(N'-methyl-iN'-n- brity 1-aminoätlry 1) - amid-N'-methy 1-N'-methan- sulfonat bildet weisse, hygroskopische, leicht wasserlösliche Kristalle, die sich beim Erhitzen über 85 langsam zersetzen.
<I>Beispiel:</I> o<B>39,9</B> ; Nicotillsäure-N-(1,2-diphenyl-ätliy#1)- -(N'-niethyl-N'-n-butyl:-aminoäthy 1)-amid erden in 250 Gina Essigester gelöst und mit 11,0 g llethansulfonsäure-methylester versetzt. Das Reaktionsgemisch wird 2 Stunden unter Rühren auf 80-90 erhitzt. Nach dem Abküh len wird mit 500 ema Wasser versetzt, mit Kohle filtriert und bei 60-65 das Nasser ab destilliert.
Der Riiekstand wird 24. Stunden bei 40-45 über Phosphorpentoxyd getrocknet, in Chloroform gelöst, filtriert und mit abs. Äther gefällt.
Mit dem erhaltenen Produkt wird die ganze Reinigungsprozedur vorzugsweise wiederholt, wobei Nicotinsä.ure-N-(1,2-(liphenyl-äthyl)-N- (N'- methyl-N'- n-buty 1- aminoäthyl ) - amid - N'- lnethyl-N'-methansulfonat. in guter Ausbeute gewonnen wird. Die neue Verbindung bildet weisse, hygroskopische, leicht wasserlösliche Kristalle. die sich beim Erhitzen über 85 langsam zersetzen.
Process for the preparation of a new quaternary salt. The invention relates to a process for the preparation of a new quaternary salt of the formula
EMI0001.0005
which is characterized in that the compound of the formula
EMI0001.0006
quaternized with methyl methanesulfonate.
The conversion takes place preferably in the presence of a solvent or diluent.
When using 1 mole of methanesulfone-s', es-e-niethyl ester to 1 mole of compound I, the observation was made that the tertiary nitrogen atom of the side chain is quaternized before the nitrogen atom of the pyridine ring.
It is important not to work with too large an excess of methyl methanesulfonate, otherwise there is a risk that the pyridine nitrogen atom will also be quaternized. The nicotinic acid (1,2-diphenyl-aryl) -1- (N'-methyl-iN'-n-brity 1-aminoethyl 1) amide-N'-methy 1-N'-methanesulfonate obtained in this way white, hygroscopic, easily water-soluble crystals that slowly decompose when heated above 85.
<I> Example: </I> o <B> 39.9 </B>; Nicotillic acid-N- (1,2-diphenyl-ätliy # 1) - - (N'-niethyl-N'-n-butyl: -aminoethy 1) -amide dissolved in 250 gina ethyl acetate and mixed with 11.0 g of methanesulfonic acid methyl ester added. The reaction mixture is heated to 80-90 for 2 hours with stirring. After cooling down, 500 ema water is added, the mixture is filtered with charcoal and the water is distilled off at 60-65.
The residue is dried over phosphorus pentoxide for 24 hours at 40-45 hours, dissolved in chloroform, filtered and washed with abs. Ether pleases.
The entire cleaning procedure is preferably repeated with the product obtained, with nicotinic acid-N- (1,2- (liphenyl-ethyl) -N- (N'-methyl-N'- n-buty 1- aminoethyl) - amide - N'-ethyl-N'-methanesulfonate. Is obtained in good yield. The new compound forms white, hygroscopic, easily water-soluble crystals, which slowly decompose when heated above 85 °.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297736T | 1951-03-01 | ||
| CH297741T | 1951-03-01 | ||
| CH294512T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297736A true CH297736A (en) | 1954-03-31 |
Family
ID=27178212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297736D CH297736A (en) | 1951-03-01 | 1951-03-01 | Process for the preparation of a new quaternary salt. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297736A (en) |
-
1951
- 1951-03-01 CH CH297736D patent/CH297736A/en unknown
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