CH302829A - Process for the production of a new basic ether. - Google Patents
Process for the production of a new basic ether.Info
- Publication number
- CH302829A CH302829A CH302829DA CH302829A CH 302829 A CH302829 A CH 302829A CH 302829D A CH302829D A CH 302829DA CH 302829 A CH302829 A CH 302829A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- new basic
- basic ether
- ether
- phenoxy
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 210000000653 nervous system Anatomy 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen hasischen Äthers. Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen basischen Äthers der Formel
EMI0001.0003
welches dadurch gekennzeichnet ist, dass man auf 1-(2'-Oxy-phenoxy)-2-oxo-propan Hy- droxylamin einwirken lässt und das entstan dene Oxim reduziert. Das so erhaltene 1-(2'- Oxy-phenoxy)-2-amino-propan bildet farblose Kristalle, die bei 110-11411 unter Zersetzung schmelzen. Das Hydrochlorid der Base sehmilzt bei 207-208 .
Der neue basische Äther beein flusst .das vegetative Nervensystem. Er soll deshalb als Arzneimittel, ausserdem aber auch als Zwischenprodukt zur Herstellung der N- Alkylderivate Verwendung finden.
.Beispiel: 13,3 g 1-(2'-Oxy-phenoxy)-2-oxo-propän- werden mit 11,1 g Hydroxylaminhydrochlorid und 15,8g Kaliumacetat in 300 em3 Wasser einige Zeit geschüttelt. Die entstandene volu minöse Fällung wird in Äther aufgenommen, die Ätherlösung getrocknet und verdampft. Das Oxim bleibt als gelbliches öl zurück. Die ses wird in 160 cm3 Äthanol gelöst und mit Raney-Nickel im Autoklaven bei 150 at hy driert.
Nach dem Abfiltrieren des Katalysa- tors wird das Filtrat im Vakuum einge dampft. :Der Rückstand, bestehend aus 1-(2' Oxy-phenoxy)-2-amino-propan, schmilzt bei 110-11411 unter Zersetzung. Das Hydrochlo- rid der Base zeigt aus Äthanol umkristalli siert einen Schmelzpunkt von 207-208 .
Process for the production of a new hasic ether. The present patent relates to a process for the preparation of a new basic ether of the formula
EMI0001.0003
which is characterized in that 1- (2'-oxy-phenoxy) -2-oxo-propane hydroxylamine is allowed to act and the resulting oxime is reduced. The 1- (2'-oxyphenoxy) -2-aminopropane thus obtained forms colorless crystals which melt at 110-11411 with decomposition. The base hydrochloride melts at 207-208.
The new basic ether influences the vegetative nervous system. It should therefore be used as a drug, but also as an intermediate for the preparation of N-alkyl derivatives.
Example: 13.3 g of 1- (2'-oxy-phenoxy) -2-oxo-propane are shaken with 11.1 g of hydroxylamine hydrochloride and 15.8 g of potassium acetate in 300 cubic meters of water for some time. The resulting voluminous precipitate is absorbed in ether, the ether solution is dried and evaporated. The oxime remains as a yellowish oil. This ses is dissolved in 160 cm3 of ethanol and hydrated with Raney nickel in an autoclave at 150 atm.
After the catalyst has been filtered off, the filtrate is evaporated in vacuo. : The residue, consisting of 1- (2 'oxy-phenoxy) -2-aminopropane, melts at 110-11411 with decomposition. The hydrochloride of the base, recrystallized from ethanol, has a melting point of 207-208.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292589T | 1950-04-06 | ||
| CH302829T | 1952-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302829A true CH302829A (en) | 1954-10-31 |
Family
ID=25733285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302829D CH302829A (en) | 1950-04-06 | 1952-02-26 | Process for the production of a new basic ether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302829A (en) |
-
1952
- 1952-02-26 CH CH302829D patent/CH302829A/en unknown
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