CH297739A - Process for the preparation of a new quaternary salt. - Google Patents
Process for the preparation of a new quaternary salt.Info
- Publication number
- CH297739A CH297739A CH297739DA CH297739A CH 297739 A CH297739 A CH 297739A CH 297739D A CH297739D A CH 297739DA CH 297739 A CH297739 A CH 297739A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- quaternary salt
- new
- new quaternary
- formula
- 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 4
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims description 4
- -1 1,2 diphenyl-ethyl Chemical group 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- 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
EMI0001.0007
welches dadurch gekennzeichnet ist., dass man die Verbindung der Formel
EMI0001.0008
tnit Methansulfonsäure-methylester quaterni- siert.
Der Umsatz geschieht vorzugsweise in An wesenheit eines Lösungs- bzw. Verdünnungs- tuittels.
Bei Verwendung von 1 Mol Methansulfon- säure-methylester auf 1 Mol der Verbindung I wurde die Beobachtung gemacht, dass das tertiäre Stickstoffatom der Seitenkette vor dem Stickstoffatom des Pyridinringes quater- nisiert wird. Es ist wichtig, da.ss man nicht mit einem zu grossen Mersehuss an Methan sulfonsäure-methylester arbeitet, da sonst die Gefahr besteht, dass das Pvridinstickstoffatom auch quaternisiert wird.
Das so erhaltene N icotinsäure--NT- (1, 2-diphenyl-äthyl) - N- (N'-di- isopropyl. - a minopropy 1) - amid - N'- methyl - N'- methansulfonat bildet- weisse, hygroskopische, leicht wasserlösliche Kristalle, die sieh beim Erhitzen über 1.00 langsam zersetzen.
Beispiel: 42,7 g Nicotinsäure-N-(1,2-diplienyl-ätliyl)- N-(N'-diisopropyl-aminopropyl)-amid werden in 250 ema Essigester gelöst. und mit 11,O <B>g</B> MethansulfonsäLire-methvlester versetzt. Das Reaktionsgemisch wird 2 Stunden. unter Rüh ren auf 80-90 erhitzt. Nach dem Abkühlen wird mit 500 ein a Wasser versetzt, ausgeä.thert, mit.
Kohle filtriert und bei 60-6i das Was- ser abdestilliert. Der Rückstand wird 24 Stun den bei 30-40 über Phosphorpentozyd ge trocknet, in Chloroform gelöst, filtriert und mit abs. Ather cefällt..
Mit dem erhaltenen Produkt wird die nze Reinigungsprozedur wiederholt, \wobei Nieot.insäure-N-(1,2-diphenyl-äthyl ?-N -(N'- diisopropyl-amin.opropi-l )-amid-N'-methyl-N'- methabsulfonat in guten Aasbeute gewonnen wird.
Die neue V erbindung- bildet weisse, hy- groskopisehe, leicht. wasserlösliche Kristalle, die sieh beim Erhitzen. über 100 lan;sam zersetzen.
Process for the preparation of a new quaternary salt. The subject of the invention is. a process for the preparation of a new quaternary salt of the formula
EMI0001.0007
which is characterized. That one the compound of the formula
EMI0001.0008
Quaternized with methanesulfonic acid methyl ester.
The conversion takes place preferably in the presence of a solvent or diluent.
When using 1 mole of methyl methanesulfonate 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 that you do not work with too much methane sulfonic acid methyl ester, as otherwise there is a risk that the pyridine nitrogen atom will also be quaternized.
The nicotinic acid thus obtained - NT- (1,2-diphenyl-ethyl) - N- (N'-diisopropyl. - a minopropy 1) - amide - N'-methyl - N'-methanesulfonate forms white, hygroscopic, easily water-soluble crystals that slowly decompose when heated above 1.00.
Example: 42.7 g of nicotinic acid-N- (1,2-diplienyl-ethyl) -N- (N'-diisopropyl-aminopropyl) -amide are dissolved in 250 ema ethyl acetate. and mixed with 11.0 g MethanesulfonsäLire-Methvlester. The reaction mixture is 2 hours. heated to 80-90 with stirring. After cooling, 500 a of water is added, etherified, with.
Filtered charcoal and distilled off the water at 60-6 l. The residue is dried over phosphorus pentozyd for 24 hours at 30-40, dissolved in chloroform, filtered and washed with abs. Ather falls ..
The new cleaning procedure is repeated with the product obtained, with Nieot.insäure-N- (1,2-diphenyl-ethyl? -N - (N'- diisopropyl-amin.opropi-1) -amid-N'-methyl- N'-methabsulfonate is obtained in good carcass yield.
The new connection - forms white, hygroscopic, light. water-soluble crystals that see when heated. decompose over 100 lan; sam.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294512T | 1951-03-01 | ||
| CH297739T | 1951-03-01 | ||
| CH297741T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297739A true CH297739A (en) | 1954-03-31 |
Family
ID=27178215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297739D CH297739A (en) | 1951-03-01 | 1951-03-01 | Process for the preparation of a new quaternary salt. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297739A (en) |
-
1951
- 1951-03-01 CH CH297739D patent/CH297739A/en unknown
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