CH291937A - Process for the preparation of a new thioether. - Google Patents
Process for the preparation of a new thioether.Info
- Publication number
- CH291937A CH291937A CH291937DA CH291937A CH 291937 A CH291937 A CH 291937A CH 291937D A CH291937D A CH 291937DA CH 291937 A CH291937 A CH 291937A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- dimethylamino
- thioether
- phenyl
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000003568 thioethers Chemical class 0.000 title claims description 5
- -1 ethyl compound Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- RHSQKVNZYFWQDS-UHFFFAOYSA-N CN(CCC(CCSC)(CN)C1=CC=CC=C1)C Chemical compound CN(CCC(CCSC)(CN)C1=CC=CC=C1)C RHSQKVNZYFWQDS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
<B>verfahren</B> zur <B>Herstellung</B> eines <B>neuen</B> Thioäthers. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Thioäthers, nämlich des 1.-Dimethylamino- 3 - aminoinethyl - 3-phenyl-5-methylmercapto- pentans.
Dieser neue Äther soll als Zwischen pro < lukt zur Herstellung von analgetisch und antiallergisch wirkenden Verbindungen ver wendet werden.
Das den Gegenstand des Patentes bildende Verfahren ist dadurch gekennzeichnet, dass man die Verbindung der Formel
EMI0001.0011
reduziert. Die Reduktion kann in bekannter Weise mit nascierenden oder katalytisch aktiviertem Wasserstoff erfolgen. Als sehr vorteilhaft hat sieh die Reduktion mit Lithiumaluminium- liydrid in Äther erwiesen. Das in dieser Weise erhaltene 1-Dimethylamino-3-aminomethyl-3- pheny 1-5-methylmercapto-pentan bildet ein unter 0,02 mm bei 126-127 siedendes hell gelbes öl. Seine N-Acetylverbindung schmilz bei 50 .
Beispiel: 30 g 1-Dimethylamino-3-cyano-3-phenyl-5- metliyimercapto-pentan, gelöst in 150 cms abs. Äther, werden unter Turbinieren mit einer Suspension von 10,4 g Lithiumaluminium- hydrid in 200 em3 abs. Äther tropfenweise versetzt. Nach 24 Stunden wird vorsichtig mit Wasser versetzt, bis der Lithiumaluminium- hydrid-Überschuss zersetzt ist und dann 100 cm3 2n-Essigsäure zugegeben.
Von die sem Gemisch wird der Äther abdestilliert und die wässrige Lösung mit konz. Natronlauge alkalisiert. Die ölige Ausscheidung wird in Äther aufgenommen und die vereinigten Ätherextrakte getrocknet und verdampft. Der Rückstand wird im Hochvakuum destilliert.
Klan erhält so 26 g des unter 0,02 mm bei 126-127 siedenden 1-Dimethylamino-3-amino- methyl - 3 - phenyl - 5 -methylmercapto-pentans. Die neue Base ist wenig löslich in Wasser, gut löslich in den gebräuchlichen organischen Lösungsmitteln. Die N - Acetylverbindung schmilzt bei 50 .
<B> process </B> for <B> production </B> of a <B> new </B> thioether. The subject of the present patent is a process for the production of a new thioether, namely 1.-dimethylamino-3-aminoinethyl-3-phenyl-5-methylmercaptopentane.
This new ether is to be used as an intermediate product for the production of compounds with an analgesic and antiallergic effect.
The process forming the subject of the patent is characterized in that the compound of the formula
EMI0001.0011
reduced. The reduction can take place in a known manner with nascent or catalytically activated hydrogen. The reduction with lithium aluminum hydride in ether has proven to be very advantageous. The 1-dimethylamino-3-aminomethyl-3-pheny 1-5-methylmercapto-pentane obtained in this way forms a pale yellow oil boiling below 0.02 mm at 126-127. Its N-acetyl compound melts at 50.
Example: 30 g of 1-dimethylamino-3-cyano-3-phenyl-5-methylimercapto-pentane, dissolved in 150 cms of abs. Ether, are turbinated with a suspension of 10.4 g of lithium aluminum hydride in 200 em3 abs. Ether added dropwise. After 24 hours, water is carefully added until the excess lithium aluminum hydride has decomposed and 100 cm3 of 2N acetic acid are then added.
From this mixture the ether is distilled off and the aqueous solution with conc. Caustic soda alkalizes. The oily excretion is taken up in ether and the combined ether extracts are dried and evaporated. The residue is distilled in a high vacuum.
Klan thus receives 26 g of 1-dimethylamino-3-aminomethyl-3-phenyl-5-methylmercaptopentane which boils below 0.02 mm at 126-127. The new base is sparingly soluble in water and readily soluble in common organic solvents. The N - acetyl compound melts at 50.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH291937T | 1953-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH291937A true CH291937A (en) | 1953-07-15 |
Family
ID=4487624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH291937D CH291937A (en) | 1953-08-23 | 1950-08-23 | Process for the preparation of a new thioether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH291937A (en) |
-
1950
- 1950-08-23 CH CH291937D patent/CH291937A/en unknown
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