CH169506A - Process for the preparation of 1- (3 ', 4'-ethylenedioxy) -phenyl-2-aminopropan-1-ol. - Google Patents
Process for the preparation of 1- (3 ', 4'-ethylenedioxy) -phenyl-2-aminopropan-1-ol.Info
- Publication number
- CH169506A CH169506A CH169506DA CH169506A CH 169506 A CH169506 A CH 169506A CH 169506D A CH169506D A CH 169506DA CH 169506 A CH169506 A CH 169506A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- preparation
- sub
- ethylenedioxy
- aminopropan
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- -1 3 ', 4'-ethylenedioxy Chemical group 0.000 claims description 2
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical compound ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- MBEGNJWTCXYTKP-UHFFFAOYSA-N 1,4-dioxan-2-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1COCCO1 MBEGNJWTCXYTKP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- YJPPMRXJRCEKFA-UHFFFAOYSA-N ClO.CCCO Chemical compound ClO.CCCO YJPPMRXJRCEKFA-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 1-(3',4'-Äthylendiogy)-phenyl-2-aminopropan-l-ol. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1-(3',4' Äthylendioxy) - phenyl -2 - aminopropan -1- o1, welches dadurch gekennzeichnet ist, dass man auf 3,4-Äthylendioxypropiopherron salpetrige Säure einwirken lässt und das so erhaltene Isonitrosoketon mit reduzierenden Mitteln be handelt.
Die neue Verbindung bildet ein in Wasser und Alkohol lösliches Chlorhydrat vom Schmelzpunkt 213 C ; sie besitzt eine starke Uteruswirkung und kann entsprechende Ver wendung in der Therapie finden.
<I>Beispiel:</I> 19,2 gr 3,4 - Äthylendioxypropiophenon werden in 200 cm' Benzol gelöst und mit 10,3 gr Butylnitrit versetzt. Zu der erhaltenen Lösung werden 15 gr einer 30 /oigen äthe rischen Salzsäure hinzugetropft. Die Flüssig keit bleibt über Nacht stehen. Das auskristal lisierende Produkt wird abgesaugt und mit Benzol nachgewaschen.
Das entstandene 3,4- Äthyler)dioxyisonitrosopropiopherion schmilzt nach dem Umkristallisieren aus Benzol bei 142-143 . 14 gr der umkristallisierten Iso- nitrosoverbindung werden in 200 cm' Alkohol gelöst und mit Wasserstoff und Nickel bei <B>70'</B> hydriert. Nach Aufnahme der berechne ten Menge Wasserstoff wird vom Nickel katalysator abgesaugt und der überschüssige Alkohol im Vakuum entfernt. Der verblei bende Rückstand wird mit alkoholischer Salz säure neutralisiert und durch Zugabe von Aceton das Chlorhydrat ausgefällt.
Das 3,4 Äthylendioxyphenylamir)opropanolchlorhydrat schmilzt nach dem Unikristallisieren aus Alko hol bei 213 C.
Process for the preparation of 1- (3 ', 4'-ethylenediogy) -phenyl-2-aminopropan-1-ol. The present invention relates to a process for the preparation of 1- (3 ', 4' ethylenedioxy) - phenyl -2 - aminopropane -1- o1, which is characterized in that nitrous acid is allowed to act on 3,4-ethylenedioxypropiopherron and that Isonitrosoketone thus obtained is treated with reducing agents.
The new compound forms a hydrochloride, soluble in water and alcohol, with a melting point of 213 C; it has a strong uterine effect and can be used appropriately in therapy.
<I> Example: </I> 19.2 grams of 3,4 - ethylenedioxypropiophenone are dissolved in 200 cm of benzene and mixed with 10.3 grams of butyl nitrite. 15 g of a 30% ethereal hydrochloric acid are added dropwise to the resulting solution. The liquid stays there overnight. The crystallizing product is filtered off and washed with benzene.
The 3,4-ethyl) dioxyisonitrosopropiopherion formed melts at 142-143 after recrystallization from benzene. 14 g of the recrystallized isonitroso compound are dissolved in 200 cm 'of alcohol and hydrogenated with hydrogen and nickel at <B> 70' </B>. After the calculated amount of hydrogen has been absorbed, the nickel catalyst is sucked off and the excess alcohol is removed in vacuo. The remaining residue is neutralized with alcoholic hydrochloric acid and the hydrochloride is precipitated by adding acetone.
The 3,4 ethylenedioxyphenylamir) propanol chlorohydrate melts after unicrystallization from alcohol at 213 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169506X | 1931-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169506A true CH169506A (en) | 1934-05-31 |
Family
ID=5687866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169506D CH169506A (en) | 1931-09-16 | 1932-09-14 | Process for the preparation of 1- (3 ', 4'-ethylenedioxy) -phenyl-2-aminopropan-1-ol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169506A (en) |
-
1932
- 1932-09-14 CH CH169506D patent/CH169506A/en unknown
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