DE2022926C3 - Process for the preparation of lumilysergic acid alkyl esters - Google Patents
Process for the preparation of lumilysergic acid alkyl estersInfo
- Publication number
- DE2022926C3 DE2022926C3 DE19702022926 DE2022926A DE2022926C3 DE 2022926 C3 DE2022926 C3 DE 2022926C3 DE 19702022926 DE19702022926 DE 19702022926 DE 2022926 A DE2022926 A DE 2022926A DE 2022926 C3 DE2022926 C3 DE 2022926C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- acid alkyl
- alkyl esters
- lumilysergic
- lumilysergic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 title claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- -1 lysergic acid monohydrate Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Description
in der R eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen darstellt, dadurch gekennzeichnet, daß Lysergsäure mit einem gesättigten aliphatischen Alkohol mit 1 bis 4 Kohlenstoffatomen bei einer Temperatur von O bis 400C in Gegenwart von Licht und reiner Schwefelsäure umgesetzt wird.in which R represents an alkyl group with 1 to 4 carbon atoms, characterized in that lysergic acid is reacted with a saturated aliphatic alcohol with 1 to 4 carbon atoms at a temperature of 0 to 40 ° C. in the presence of light and pure sulfuric acid.
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von Lumilysergsäurealkylesterderivaten der allgemeinen FormelThe invention relates to a process for the preparation of alkyl lumilysergic acid derivatives the general formula
COORCOOR
RO -y RO -y
N-CH3 N-CH 3
3535
4040
in der R eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen darstellt.in which R represents an alkyl group having 1 to 4 carbon atoms.
Die erfindungsgemäß hergestellten Produkte werden als Ausgangsprodukte für pharmakologisch aktive Verbindungen, die in der USA-Patentschrift 32 28 943 beschrieben sind, verwendetThe products according to the invention are used as starting materials for pharmacologically active Compounds described in U.S. Patent 3,228,943 were used
Das erfindungsgemäße Verfahren besteht darin, daß Lysergsäure mit einem gesättigten aliphatischen Alkohol mit 1 bis 4 Kohlenstoffatomen bei einer Temperatur von 0 bis 400C in Gegenwart von Licht und reiner Schwefelsäure umgesetzt wird.The process according to the invention consists in that lysergic acid is reacted with a saturated aliphatic alcohol having 1 to 4 carbon atoms at a temperature of 0 to 40 ° C. in the presence of light and pure sulfuric acid.
Diese Reaktion bewirkt die Addition eines Alkohols an die Doppelbindung in 9-,10-Stellung, wobei gleichzeitig die Carboxylgruppe in 8-Stellung verestert wird.This reaction causes the addition of an alcohol to the double bond in the 9-, 10-position, whereby at the same time the carboxyl group in the 8-position is esterified.
Als Lichtquelle kann eine normale UV-Lampe oder Sonnenlicht verwendet werden.A normal UV lamp or sunlight can be used as the light source.
Die Reaktion wird vorzugsweise von 100C bis Raumtemperatur durchgeführtThe reaction is preferably carried out from 10 ° C. to room temperature
Wenn die Reaktion vorbei ist, d. h. be»m Verschwinden des für Lysergderivate charakteristischen Maximums bei 315 ΐημ im Absorptionsspektrum, wird die Mischung mit Ammoniak alkalisch gemacht und dann mit einem mit Wasser nicht mischbaren Lösungsmittel extrahiert, wie z.B. Äthylacetat oder Chloroform. Danach wird das Lösungsmittel abgedampft und das Reaktionsprodukt aus einem geeigneten Lösungsmittel kristallisiertWhen the reaction is over i. H. be gone of the maximum characteristic of Lyserg derivatives at 315 ΐημ in the absorption spectrum, the Mixture made alkaline with ammonia and then with a water immiscible solvent extracted, such as ethyl acetate or chloroform. Then the solvent is evaporated and the Reaction product crystallized from a suitable solvent
Das folgende Beispiel soll die vorliegende Erfindung näher erläutern.The following example is intended to explain the present invention in more detail.
Beispiel
8-Methylester-lO-methyläther der Lumilysergsäureexample
8-methyl ester-10-methyl ether of lumilysergic acid
1,5 g Lysergsäuremonohydrat werden in 40 ml Methanol und 7,5 ml Schwefelsäure gelöst; die erhaltene Mischung wird in einem Kolben aus wärmebeständigem Borosilikatglas mit einer fluoreszierenden Quecksilberlichtlampe von 250 Watt bestrahlt. Wenn die Reaktion vorbei ist, wird die Mischung mit Wasser verdünnt, mit Ammoniak alkalisch gemacht und mit Chloroform extrahiert1.5 g of lysergic acid monohydrate are dissolved in 40 ml of methanol and 7.5 ml of sulfuric acid; the received Mixture is placed in a flask made of heat-resistant borosilicate glass with a fluorescent mercury lamp irradiated by 250 watts. When the reaction is over, the mixture is diluted with water, using Ammonia made alkaline and extracted with chloroform
Nach Abdampfen des Lösungsmittels und Kristallisieren aus Äthyläther werden 1,1 g 8-Methylester-lO-methyläther der Lumilysergsäure mit einem Schmelzpunkt von 181 bis 1830C erhalten; [λ] Γ= 0° (c = 0,47 in Pyridin).After evaporation of the solvent and crystallization from ethyl ether, 1.1 g of 8-methyl ether-Methylester lO-get the Lumilysergsäure having a melting point 181-183 0 C; [λ] Γ = 0 ° (c = 0.47 in pyridine).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1676269 | 1969-05-13 | ||
| IT1676269 | 1969-05-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2022926A1 DE2022926A1 (en) | 1970-11-19 |
| DE2022926B2 DE2022926B2 (en) | 1977-05-26 |
| DE2022926C3 true DE2022926C3 (en) | 1978-01-19 |
Family
ID=
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