CH96606A - Process for the preparation of a basic derivative of p-aminophenol ethyl ether. - Google Patents
Process for the preparation of a basic derivative of p-aminophenol ethyl ether.Info
- Publication number
- CH96606A CH96606A CH96606DA CH96606A CH 96606 A CH96606 A CH 96606A CH 96606D A CH96606D A CH 96606DA CH 96606 A CH96606 A CH 96606A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl ether
- aminophenol
- preparation
- basic derivative
- water
- Prior art date
Links
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical class CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims description 3
- KSDPEFVRNOACII-UHFFFAOYSA-N N-[2-(2-piperidin-1-ylethoxy)phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=CC=C1)OCCN1CCCCC1 KSDPEFVRNOACII-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- -1 halogen ethyl ether Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines basischen Derivates des p-Aminophenoläthylätliers. Es wurde gefunden, dass man zu einem basischen Derivate des p-Aminophenoläthyl- äthers gelangen kann, indem man p-Acet- aminoplienolhalogenäthyläther mit Piperidin umsetzt.
Der so erhaltene Acetaminophenol-ss-pi- peridyläthyläther bildet neutral reagierende, farblose, .wasserlösliche Salze. Das Chlor hydrat zum Beispiel stellt in Wasser leicht lösliche Kristalle vom Schmelzpunkt<B>252'</B> dar.
Die neue Verbindung soll zu therapeu tischen Zwecken verwendet werden. Beispiel: 10 Teile Acetaminoplienol-p-broniäthyl- äther werden mit 10 Teilen Piperidin und etwas Alkohol 3 Stunden am Wasserbad erhitzt. Dann giesst man in 200 Teile Wasser und zieht zweimal mit Äther aus. Der Äther wird zur Entfernung von Piperidin einige Mal mit frischem Wasser durchgeschüttelt und hierauf mit Ca0ls getrocknet.
Man ver- setzt dann die ätherische Lösung mit alko holischer Salzsäure, worauf das Chlorbydrat des Acetaminophenol-p-piperidinäthyläthers ausfällt, das _ man aus wenig Wasser um kristallisiert
Process for the preparation of a basic derivative of p-Aminophenoläthylätliers. It has been found that a basic derivative of p-aminophenol ethyl ether can be obtained by reacting p-acetaminoplienol halogen ethyl ether with piperidine.
The acetaminophenol-β-piperidylethyl ether obtained in this way forms colorless, water-soluble salts with a neutral reaction. The chlorine hydrate, for example, is easily soluble in water crystals with a melting point of <B> 252 '</B>.
The new compound is intended to be used for therapeutic purposes. Example: 10 parts of acetaminoplienol-p-broniäthylether are heated with 10 parts of piperidine and a little alcohol for 3 hours on a water bath. Then it is poured into 200 parts of water and extracted twice with ether. The ether is shaken a few times with fresh water to remove the piperidine and then dried with CaOls.
The ethereal solution is then mixed with alcoholic hydrochloric acid, whereupon the chlorine hydrate of acetaminophenol-p-piperidine ethyl ether precipitates, which is recrystallized from a little water
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH96389T | 1921-06-04 | ||
| CH96606T | 1921-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH96606A true CH96606A (en) | 1922-11-01 |
Family
ID=25705085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH96606D CH96606A (en) | 1921-06-04 | 1921-06-04 | Process for the preparation of a basic derivative of p-aminophenol ethyl ether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH96606A (en) |
-
1921
- 1921-06-04 CH CH96606D patent/CH96606A/en unknown
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