CH163397A - Process for the preparation of 1-p-oxyphenyl-2-N-methyl-amino-ethanol-1. - Google Patents
Process for the preparation of 1-p-oxyphenyl-2-N-methyl-amino-ethanol-1.Info
- Publication number
- CH163397A CH163397A CH163397DA CH163397A CH 163397 A CH163397 A CH 163397A CH 163397D A CH163397D A CH 163397DA CH 163397 A CH163397 A CH 163397A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- substance
- carrying substance
- ethanol
- carrying
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002269 analeptic agent Substances 0.000 claims description 2
- 230000003555 analeptic effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 10
- 238000009835 boiling Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000005526 vasoconstrictor agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung von 1-p-Oxyphenyl-2-lV-metliyl-ainino-äthanol-1. Die Erfindung betrifft ein Verfahren zur Herstellung von 1-p-Oxyphenyl-2-N-methyl- arnirio-äthanol-1 vom F.
P. 15ä-156 einer Verbindung, die durch wertvolle therapeutische Eigenschaften, insbesondere durch adrenalin- artige, vorzugsweise analeptische und vaso- konstriktorischeWirkungen auch bei peroraler Darreichung, bei geringerer Giftigkeit wie das Adrenalin, ausgezeichnet ist und auch bei wiederholtem Kochen ihrer wässerigen Lösung zwecks Sterilisierung ihre Wirksamkeit nicht verliert.
Diese Verbindung wird erfindungsgemäss erhalten, indem man auf co-Methylamino-p- oxy-acetopbenon von der Formel:
EMI0001.0015
Wasserstoff bei Gegenwart von Wasserstoff übertragenden Katalysatoren, wie Palladium oder anderen Metallen der Platingrüppe, Platinoxyd, Nickel usw. einwirken lässt.
Die Katalysatoren sind vorteilhaft im Zustande feiner, vorzugsweise kolloidaler Verteilung anzuwenden; gegebenenfalls in Verbindung mit geeigneten Trägern, wie Kohle, Bariumsulfat, Kieselgur usw., z. B. in Form von auf Kohle oder Bariumsulfat niedergeschlagenem, feinverteiltem Palladium, während das cu-Methylamino-p-oxy-acetophe- non in einem geeigneten wässerigen oder nicht wässerigen Lösungsmittel, wie Wasser, Alkohol, Methylalkohol usw. der Reaktion unterworfen werden kann.
Die Einwirkung des Wasserstoffes kann je nach der Art des Katalysators oder der sonstigen Arbeits bedingungen, der Anwendungsform der Aus gangsstoffe, der Art des Lösungsmittels, der Temperatur usw., sowohl bei gewöhnlichem als auch bei erhöhtem Druck erfolgen.
Die bei dem Verfahren erzielbaren Aus beuten sind z. B. abhängig von der Natur des Lösungsmittels, de;' Art und Menge des verwendeten Katalysators usw.
Dass das 1-p-Oxyphenyl-2-N-methylamino- äthanol-1 die oben erwähnten therapeutisch wertvollen Eigenschaften zeigt, musste über raschen, weil man bisher annahm, dass solche Eigenschaften nur den Brenzkatechinderivaten zukommen könnten, während es anderseits bekannt ist, dass ähnlich konstituierte, aber eine Hydroxylgruppe nicht enthaltende Ver bindungen selbst in starker Konzentration Anämie kaum erzeugen.
<I>Beispiel:</I> 10 gr m-I\tethylamino-p-oxy-acetophenon werden in 200 cm' Methanol gelöst und nach Zugabe von 2,5 gr Palladiumkatalysator mit Wasserstoff geschüttelt. Nach Aufnahme der für die Reduktion der Ketogruppe erforder lichen Menge Wasserstoff wird vom Kataly sator abgesaugt und das Filtrat im Vakuum zur Trockne gedampft. Der hinterbleibende Rückstand, aus Alkohol umkristallisiert, ist reines 1-p-Oxy-phenyl-2-N-methylamino-ätha- nol-l. Ausbeute 95% d. Th.
Process for the preparation of 1-p-oxyphenyl-2-IV-methyl-ainino-ethanol-1. The invention relates to a process for the preparation of 1-p-oxyphenyl-2-N-methyl-arnirio-ethanol-1 from F.
P. 15-156 of a compound which is distinguished by valuable therapeutic properties, in particular by adrenaline-like, preferably analeptic and vaso-constrictive effects, even when administered orally, with less toxicity than adrenaline, and also when its aqueous solution is repeatedly boiled for sterilization does not lose its effectiveness.
According to the invention, this compound is obtained by reacting to co-methylamino-p-oxy-acetopbenone of the formula:
EMI0001.0015
Lets hydrogen act in the presence of hydrogen-transferring catalysts, such as palladium or other metals of the platinum group, platinum oxide, nickel, etc.
The catalysts are advantageously to be used in the state of fine, preferably colloidal, distribution; optionally in conjunction with suitable carriers such as carbon, barium sulfate, diatomaceous earth, etc., e.g. B. in the form of precipitated on carbon or barium sulfate, finely divided palladium, while the cu-methylamino-p-oxy-acetophenon in a suitable aqueous or non-aqueous solvent such as water, alcohol, methyl alcohol, etc. can be subjected to the reaction.
The action of the hydrogen can take place, depending on the type of catalyst or other working conditions, the application form of the starting materials, the type of solvent, the temperature, etc., both at normal and at elevated pressure.
The recoverable from the process are z. B. depending on the nature of the solvent, de; ' Type and amount of catalyst used, etc.
The fact that 1-p-oxyphenyl-2-N-methylaminoethanol-1 shows the therapeutically valuable properties mentioned above had to come as a surprise, because it was previously assumed that such properties could only be attributed to the catechol derivatives, while on the other hand it is known that Similarly constituted, but not containing a hydroxyl group, compounds hardly produce anemia even in high concentrations.
<I> Example: </I> 10 grams of methylamino-p-oxy-acetophenone are dissolved in 200 cm of methanol and, after adding 2.5 grams of palladium catalyst, shaken with hydrogen. After the amount of hydrogen required for the reduction of the keto group has been taken up, the catalyst is suctioned off and the filtrate is evaporated to dryness in vacuo. The residue that remains, recrystallized from alcohol, is pure 1-p-oxy-phenyl-2-N-methylamino-ethanol-1. Yield 95% of theory Th.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH163397T | 1930-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH163397A true CH163397A (en) | 1933-08-15 |
Family
ID=4416448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH163397D CH163397A (en) | 1930-04-23 | 1930-04-23 | Process for the preparation of 1-p-oxyphenyl-2-N-methyl-amino-ethanol-1. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH163397A (en) |
-
1930
- 1930-04-23 CH CH163397D patent/CH163397A/en unknown
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