CH297731A - Process for the preparation of a new quaternary salt. - Google Patents
Process for the preparation of a new quaternary salt.Info
- Publication number
- CH297731A CH297731A CH297731DA CH297731A CH 297731 A CH297731 A CH 297731A CH 297731D A CH297731D A CH 297731DA CH 297731 A CH297731 A CH 297731A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- quaternary salt
- 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
- 239000000843 powder Substances 0.000 claims description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 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
- 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- -1 diethylamino-propyl Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 150000001721 carbon Chemical group 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
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen quaternären Salzes. Gegenstand der Erfindung ist ein Verfahren zur Herstellung eines neuen quater- nären Salzes der Formel
EMI0001.0007
welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel
EMI0001.0008
EMI0001.0009
init <SEP> JIctliansnlfonsätire-met.hylester <SEP> quaternisiert.
Der L insatz geschieht vorzugsweise in An- wesenheit. eines LOsungs- bzw. Verdünnungs- niit.tels.
Bei Verwendung von 1 Mol 1@Ietliansulfori- ätirc-methy@ester auf 1 Mol der Verbindung I wiu#de die Beobaehtunb gemaelit, dass das ter tiäre Stickstoffatom der Seitenkette vor dem St,iekstoffatom des Pyridinringes quaternisiert wird.
Es ist wichtig, dass man nicht mit einem zu grossen L'berschuss an Methansulfonsäure- methylester arbeitet, da sonst die Gefahr be steht, dass das Pyridinstiekstoffatom auch quaternisiert wird.
Das so erhaltene Nicotin- säure -N - (1,2 - diplienyl - äthyl) - N -<B>(T-</B> diäthyl- amino-propyl) - amid-N-methyl-methansulfonat bildet ein leicht wasserlösliches, amorphes Pul-
EMI0002.0001
ver, <SEP> das <SEP> sich <SEP> beim <SEP> Erhitzen <SEP> über <SEP> 60 <SEP> langsam
<tb> zersetzt.
<tb>
<I>Beispiel:</I>
<tb> 20 <SEP> g <SEP> Nicotinsäure-N-(1,2-diplienj,.1-ätliv1) N-(3'-diätlivlamino-proptl)-aniid <SEP> -erden <SEP> in
<tb> 100 <SEP> ema <SEP> Essigester <SEP> gelöst, <SEP> und <SEP> mit <SEP> 5,4 <SEP> g <SEP> Met.han sulfonsäure-methvlester <SEP> versetzt. <SEP> Das <SEP> Reak tionsgemisch <SEP> wird <SEP> eine <SEP> Stunde <SEP> am <SEP> Rückfluss
<tb> @@-ekoelit.
<SEP> Na <SEP> eh <SEP> dein <SEP> Abkühlen <SEP> wird <SEP> mit, <SEP> <B>270</B> <SEP> ein3
<tb> Wasser <SEP> versetzt, <SEP> ausgeäthert, <SEP> mit <SEP> Kohle <SEP> fil triert <SEP> und <SEP> bei <SEP> 35 <SEP> das <SEP> Wasser <SEP> abdestilliert.
<tb> Der <SEP> Rückstand <SEP> wird <SEP> 24- <SEP> Stunden <SEP> bei <SEP> 35 <SEP> über
<tb> Phosphorpentoxcd <SEP> getrocknet, <SEP> dann <SEP> in <SEP> 200 <SEP> ema
<tb> Chloroform <SEP> aufgenommen <SEP> und <SEP> mit <SEP> 200 <SEP> em3
EMI0002.0002
Äther <SEP> versetzt. <SEP> Mit <SEP> dem. <SEP> erhaltenen <SEP> Produkt
<tb> wird <SEP> die <SEP> ganze <SEP> Reinigungsprozedur <SEP> vorzugs weise <SEP> wiederholt, <SEP> wobei <SEP> 16 <SEP> g <SEP> Nicotinsäure-N (1,2-diphen <SEP> vl-ätliyl)-N-(3'-diäthyl-ainino-l)ro py1)-aniid-N-nietlit-l-nietliansulfonat.
<SEP> in <SEP> guter
<tb> Reinheit <SEP> gewonnen <SEP> werden.
<tb>
Die <SEP> neue <SEP> Verbindung <SEP> bildet <SEP> ein <SEP> leielit <SEP> was serlöslielies, <SEP> amorphes <SEP> Pulver, <SEP> das <SEP> sieh <SEP> beim
<tb> Erhitzen <SEP> über <SEP> 60 <SEP> langsam <SEP> zersetzt.
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
EMI0001.0007
which is characterized in that the compound of the formula
EMI0001.0008
EMI0001.0009
init <SEP> JIctliansnlfonsätire-met.hylester <SEP> quaternized.
The use is preferably done in the presence. a solvent or diluent.
When using 1 mol of 1 @ Ietliansulfori- ätirc-methy @ ester to 1 mol of the compound I, the observation would be made that the tertiary nitrogen atom of the side chain is quaternized before the carbon 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 -N - (1,2 - diplienyl - ethyl) - N - <B> (T- </B> diethylamino-propyl) - amide-N-methyl-methanesulfonate obtained in this way forms a readily water-soluble, amorphous powder
EMI0002.0001
ver, <SEP> the <SEP> <SEP> slowly when <SEP> heating <SEP> over <SEP> 60 <SEP>
<tb> decomposed.
<tb>
<I> Example: </I>
<tb> 20 <SEP> g <SEP> nicotinic acid-N- (1,2-diplienj, .1-ätliv1) N- (3'-dietlivlamino-proptl) -aniid <SEP> -erden <SEP> in
<tb> 100 <SEP> ema <SEP> ethyl acetate <SEP> dissolved, <SEP> and <SEP> with <SEP> 5.4 <SEP> g <SEP> Met.han sulfonic acid methyl ester <SEP> added. <SEP> The <SEP> reaction mixture <SEP> becomes <SEP> one <SEP> hour <SEP> at the <SEP> reflux
<tb> @@ - ekoelit.
<SEP> Well <SEP> eh <SEP> your <SEP> cooling down <SEP> becomes <SEP> with, <SEP> <B> 270 </B> <SEP> on 3
<tb> Water <SEP> added, <SEP> etherified, <SEP> with <SEP> carbon <SEP> filters <SEP> and <SEP> with <SEP> 35 <SEP> the <SEP> water <SEP> distilled off.
<tb> The <SEP> backlog <SEP> is <SEP> 24- <SEP> hours <SEP> at <SEP> 35 <SEP> over
<tb> Phosphorpentoxcd <SEP> dried, <SEP> then <SEP> in <SEP> 200 <SEP> ema
<tb> Chloroform <SEP> added <SEP> and <SEP> with <SEP> 200 <SEP> em3
EMI0002.0002
Ether <SEP> displaced. <SEP> With <SEP> the. <SEP> received <SEP> product
<tb> <SEP> the <SEP> whole <SEP> cleaning procedure <SEP> is repeated, preferably <SEP>, <SEP> where <SEP> 16 <SEP> g <SEP> nicotinic acid-N (1,2-diphen <SEP> vl-ethyl) -N- (3'-diethyl-ainino-1) ro py1) -aniid-N-nietlit-1-nietliansulfonate.
<SEP> in <SEP> good
<tb> Purity <SEP> can be obtained <SEP>.
<tb>
The <SEP> new <SEP> connection <SEP> forms <SEP> a <SEP> leielit <SEP> was serlöslielies, <SEP> amorphous <SEP> powder, <SEP> the <SEP> see <SEP> at
<tb> Heating <SEP> over <SEP> 60 <SEP> slowly <SEP> decomposes.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294512T | 1951-03-01 | ||
| CH297731T | 1951-03-01 | ||
| CH297741T | 1951-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297731A true CH297731A (en) | 1954-03-31 |
Family
ID=27178207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297731D CH297731A (en) | 1951-03-01 | 1951-03-01 | Process for the preparation of a new quaternary salt. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297731A (en) |
-
1951
- 1951-03-01 CH CH297731D patent/CH297731A/en unknown
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