CH297732A - Process for the preparation of a new quaternary salt. - Google Patents
Process for the preparation of a new quaternary salt.Info
- Publication number
- CH297732A CH297732A CH297732DA CH297732A CH 297732 A CH297732 A CH 297732A CH 297732D A CH297732D A CH 297732DA CH 297732 A CH297732 A CH 297732A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- new
- quaternary salt
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003839 salts Chemical group 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- -1 1-ethvl Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JRQLBJPVSRTDBJ-WZTVWXICSA-N [1-[(3,4-dihydroxyphenyl)methyl]-7-hydroxyisoquinolin-6-yl] hydrogen sulfate;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C1=C(O)C(O)=CC=C1CC1=NC=CC2=CC(OS(O)(=O)=O)=C(O)C=C12 JRQLBJPVSRTDBJ-WZTVWXICSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate 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
- 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
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group 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
- 239000002253 acid Substances 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
- 239000000155 melt Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
verfahren zur Herstellung eines neuen quaternären Salzes. Gegenstand der Erfindung ist, ein Ver fahren zur Herstellung eines neuen quater- niii-en Salzes der Formel
EMI0001.0007
welehes dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0009
mit -AIethansulfonsäuire-methylestex# quaterni- siel't.
Der Umsatz geschieht vorzugsweise in An wesenheit eines Lösungs- bzw. Verdünnungs mittels.
Bei Verwendung von 1 31o1 Methansulfon- s iiui e .-e-nietlivlester auf 1 Mol der Verbindung I wurde die Beobachtung gemacht, dass das ter- t.iä.re Stickstoffatom der Seitenkette vor dem Stickstoffatom des Pyridinringes quaternisiert wird.
Es ist wichtig, dass man nicht mit einem zu grossen Uberschuss an Methansulfonsäure- methylester arbeitet, da sonst die Gefahr be steht, dass das andere Pyridinstiekstoffatom auch quaternisiert wird. Das so erhaltene Nico- tinsäure-N - (;1, 2-diphenyl-äthyl) -N - (2'- piperi- dino-äthyl)-amid-N-methyl-methansulfonat ist ein leicht wasserlösliches Salz, welches bei 170-l76 schmilzt.
<I>Beispiel:</I> 10 g Nicotinsäure-N-(1,2-diphenyl-äthyl)- N-(2'-piperidino-äthyl)-amidwerden in 70 em3 Essigester gelöst und mit 2,7 g Methansulfon- säure-methylester versetzt. Das Reaktionsge misch wird eine Stunde am Rückfluss gekocht.
Nach dem Abkühlen wird mit 160 cm3 Wasser versetzt, ausgeäthert, mit Kohle filtriert und bei 65 das Wasser abdestilliert. Der Rück stand wird 24 Stunden bei 60-70 über Phos- phorpentoxyd getrocknet, dann in 100 cm3 Chloroform aufgenommen und mit 200 cm3 Äther versetzt.
Mit dem erhaltenen Produkt wird die ganze Reinigungsprozedur vorzugs weise wiederholt, wobei 6,6 g NicotinsäLire-N- (1, 2-diphenyl-äthyl )- N - (2'-piperidino- äthyl) - amid-N-methyl-methansulfonat in guter Rein heit gewonnen werden. Die neue Verbindung löst sieh leieht in Wasser.
process for the production of a new quaternary salt. The invention relates to a process for the preparation of a new quaterniii-en salt of the formula
EMI0001.0007
welehes is characterized in that the compound of the formula
EMI0001.0009
with -AIethanesulfonsäuire-methylestex # quaterni- siel't.
The conversion takes place preferably in the presence of a solvent or diluent.
When using 1 31o1 methanesulfone s iiui e-e-nietlivlester to 1 mol of the 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 other pyridine nitrogen atom will also be quaternized. The thus obtained nicotinic acid-N - (; 1, 2-diphenyl-ethyl) -N - (2'-piperidino-ethyl) -amide-N-methyl-methanesulfonate is a readily water-soluble salt, which at 170- l76 melts.
<I> Example: </I> 10 g of nicotinic acid-N- (1,2-diphenyl-ethyl) -N- (2'-piperidino-ethyl) -amide are dissolved in 70 cubic meters of ethyl acetate and mixed with 2.7 g of methanesulfone acid methyl ester added. The reaction mixture is refluxed for one hour.
After cooling, 160 cm3 of water are added, the mixture is etherified, filtered with charcoal and the water is distilled off at 65. The residue is dried over phosphorus pentoxide at 60-70 hours for 24 hours, then taken up in 100 cm3 of chloroform and mixed with 200 cm3 of ether.
With the product obtained, the whole cleaning procedure is preferably repeated, with 6.6 g of NicotinsäLire-N- (1,2-diphenyl-ethyl) - N - (2'-piperidino-ethyl) - amide-N-methyl-methanesulfonate in good purity can be obtained. The new connection loosens itself in water.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294512T | 1951-03-01 | ||
| CH297732T | 1951-03-01 | ||
| CH297741T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297732A true CH297732A (en) | 1954-03-31 |
Family
ID=27178208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297732D CH297732A (en) | 1951-03-01 | 1951-03-01 | Process for the preparation of a new quaternary salt. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297732A (en) |
-
1951
- 1951-03-01 CH CH297732D patent/CH297732A/en unknown
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