CH269036A - Process for the preparation of a derivative of the lysergic acid series halogenated on the indole nitrogen. - Google Patents
Process for the preparation of a derivative of the lysergic acid series halogenated on the indole nitrogen.Info
- Publication number
- CH269036A CH269036A CH269036DA CH269036A CH 269036 A CH269036 A CH 269036A CH 269036D A CH269036D A CH 269036DA CH 269036 A CH269036 A CH 269036A
- Authority
- CH
- Switzerland
- Prior art keywords
- lysergic acid
- preparation
- methyl ester
- acid methyl
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 title description 2
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- -1 bromine lysergic acid methyl ester Chemical compound 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 4
- RNHDWLRHUJZABX-IAQYHMDHSA-N methyl (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)OC)C2)=C3C2=CNC3=C1 RNHDWLRHUJZABX-IAQYHMDHSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VPZWPHLXULLNRZ-RHSMWYFYSA-N (6aR,9R)-7,9-dimethyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@](C)(CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 VPZWPHLXULLNRZ-RHSMWYFYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QBKFLYWZRMHHRS-UHFFFAOYSA-N chloroform;1,4-dioxane Chemical compound ClC(Cl)Cl.C1COCCO1 QBKFLYWZRMHHRS-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Darstellung eines am Indolatickstoff halogenierten Derivates der Lysergsäure-Reihe. Das vorliegende Patent, betrifft ein Ver fahren zur Herstellung von Brom-lysergsäure- methylester, welches dadurch gekennzeichnet ist, dass man N-Brom-suceinimid auf Lyserg- säure-methylester einwirken lässt.
<I>Beispiel:</I> 115 mg Lysergsäure-methylester werden in 12 em3 Dioxan gelöst und die 650 C warme Lösung mit 85 mg N-Brom succinimid in 5 ein' Dioxan von 650 C versetzt; wobei sich sofort. ein roter Niederschlag ausscheidet. Das Ge misch wird noch 3 Minuten bei 60-650 gehal ten. Zur Abscheidung der rohen Reaktions produkte wird die Dioxanlösung mit 200 cm' Chloroform verdünnt und im Scheidetrichter mit natriumbicarbonathaltsgem Wasser ge waschen.
Die Chloroform Dioxan-Schicht wird abgetrennt, mit Natriumsulfat getrocknet und zur Trockne verdampft. Die rohen Reaktions produkte werden der chromatographischen Trennung unterworfen, indem sie in 5 cm3 absolutem Chloroform gelöst werden. Die Lö sung wird auf eine Säule von 20 g Alumi niumoxyd gegossen.
Bei der Entwicklung des Chromatogrammes mit absolutem Chloroform bilden sich zwei Zonen aus: eine rasch ins Filtrat wandernde, im ultravioletten Licht nur schwach leuchtende Zone 1 und eine etwas langsamer wandernde, im ultravioletten Licht intensiv fluoreszierende Zone 2, die aus etwas Ausgangsmaterial besteht.
Das Filtrat, das die Zone 1 enthält, wird zur Trockne verdampft und der Trockenrück- stand aus Benzol umkristallisiert. Es werden derbe Klötze mit 2 Mol Kristall-Benzol erhal ten, die bei 177-1780 C schmelzen.
[a] D des kristallösungsmittelfreien Präpa- rates: -I-410 (Chloroform).
gellersche Farbreaktion: wie Lysergsäure- methylester.
In methanolischer Lösung fluoresziert der Br om lysergsäure-methylester sehr schwach. Analysenwerte: C1,H1,O2N",Br ber.: C 56,50 H 4,75 N 7,76 % gef.: 57,03 4,68 7,671/o
Process for the preparation of a derivative of the lysergic acid series halogenated on the indolate nitrogen. The present patent relates to a method for the production of methyl bromolysergate, which is characterized in that N-bromosuccinimide is allowed to act on methyl lysergic acid.
<I> Example: </I> 115 mg of lysergic acid methyl ester are dissolved in 12 cubic meters of dioxane and 85 mg of N-bromosuccinimide in a dioxane of 650 C are added to the 650 C solution; being up immediately. a red precipitate separates. The mixture is kept at 60-650 for a further 3 minutes. To separate the crude reaction products, the dioxane solution is diluted with 200 cm 'chloroform and washed in a separating funnel with water containing sodium bicarbonate.
The chloroform dioxane layer is separated, dried with sodium sulfate and evaporated to dryness. The crude reaction products are subjected to chromatographic separation by dissolving them in 5 cm3 of absolute chloroform. The solution is poured onto a column of 20 g of aluminum oxide.
During the development of the chromatogram with absolute chloroform, two zones are formed: Zone 1, which migrates rapidly into the filtrate and is only weakly luminous in ultraviolet light, and Zone 2, which migrates somewhat more slowly, which is intensely fluorescent in ultraviolet light and consists of some starting material.
The filtrate, which contains zone 1, is evaporated to dryness and the dry residue is recrystallized from benzene. Sturdy blocks containing 2 mol of crystal benzene are obtained, which melt at 177-1780 C.
[a] D of the crystal solvent-free preparation: -I-410 (chloroform).
Geller's color reaction: like methyl lysergate.
In methanolic solution, the methyl bromide lysergic acid fluoresces very weakly. Analysis values: C1, H1, O2N ", Br calc .: C 56.50 H 4.75 N 7.76% found: 57.03 4.68 7.671 / o
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH263279T | 1947-07-22 | ||
| CH269036T | 1947-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH269036A true CH269036A (en) | 1950-06-15 |
Family
ID=25730617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH269036D CH269036A (en) | 1947-07-22 | 1947-07-22 | Process for the preparation of a derivative of the lysergic acid series halogenated on the indole nitrogen. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH269036A (en) |
-
1947
- 1947-07-22 CH CH269036D patent/CH269036A/en unknown
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