CH269043A - 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
- CH269043A CH269043A CH269043DA CH269043A CH 269043 A CH269043 A CH 269043A CH 269043D A CH269043D A CH 269043DA CH 269043 A CH269043 A CH 269043A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- ergotamine
- sep
- derivative
- acid series
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 title description 2
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 229960004943 ergotamine Drugs 0.000 claims description 8
- OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 claims description 6
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960002317 succinimide Drugs 0.000 claims 1
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000006227 byproduct Substances 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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Darstellung eines am Indolstickstoff halogenierten Derivates der Lysergsäure-Reihe. Das vorliegende Patent betrifft ein Ver fahren zur Darstellung von Jod=ergotamin, welches dadurch gekennzeichnet, ist, dass man auf Ergotamin N-Jod-succinimid einwirken lässt.
<I>Beispiel:</I> 500 mg am Hochvakuum getrocknetes Er gotamin werden in 30 cm3 Dioxan gelöst und mit, einer Lösung von 260 mg (1,3 Mol) N-Jod- succinimid in 10 cm3 Dioxan versetzt. Die orangefarbene Lösung wird noch 15 Minuten bei Zimmertemperatur gehalten, während wel cher Zeit sich die Lösung allmählich trübt.
Hierauf wird mit 100 cm3 Chloroform ver setzt, im Schütteltrichter mit Sodalösimg ge waschen und die an Natrlllm$lllfat getrock nete Chloroform-Dioxan-Lösung am Vakuum zur Trockne verdampft. Der Trockenrück stand wird der chromatographischen Tren nung an 40 g Aluminiumoxyd unterworfen.
Bei der Entwicklung des Chromatogram- mes mit absolutem Chloroform gehen nur Spu ren gelber Nebenprodukte ins Filtrat, wäh rend das im UV Licht nicht leuchtende Jod- ergotamin erst mit einem Gemisch von Chloro- form mit 1/2 % Alkohol ins Filtrat gewaschen wird.
Es wird so lange mit diesem Lösungs mittel eluiert, bis die etwas stärker an der Säule haftende, im UV-Licht intensiv violett leuchtende Zone im Begriffe steht, ebenfalls ins Filtrat gewaschen zu werden. Die auf .diese Weise erhaltenen 260 mg Jod-ergotamin kristallisieren aus 90 %igem Aceton in gerade abgeschnittenen Platten, die bei 1740 C untrer starker Zersetzung schmelzen und Kristallösungsmittel enthalten.
[a121 des im Hochvakuum bei 1000 ge trockneten Produktes -156o (in Chloroform).
EMI0001.0048
Kellersche <SEP> Farbreaktion: <SEP> wie <SEP> Ergotamin.
<tb> Bruttoformel: <SEP> <B>C"H34väNGJl.</B>
<tb> ber.: <SEP> C <SEP> 55,99 <SEP> H <SEP> 4,85 <SEP> N <SEP> 9,90%
<tb> gef.: <SEP> 56,29 <SEP> 5,41 <SEP> 9,92%
Process for the preparation of a derivative of the lysergic acid series halogenated on the indole nitrogen. The present patent relates to a process for the preparation of iodine = ergotamine, which is characterized in that N-iodosuccinimide is allowed to act on ergotamine.
<I> Example: </I> 500 mg erotamine dried in a high vacuum are dissolved in 30 cm3 of dioxane and mixed with a solution of 260 mg (1.3 mol) of N-iodosuccinimide in 10 cm3 of dioxane. The orange solution is kept at room temperature for a further 15 minutes, during which time the solution gradually becomes cloudy.
100 cm3 of chloroform are then added, the mixture is washed with soda solution in a separating funnel and the chloroform-dioxane solution dried on sodium chloride is evaporated to dryness in a vacuum. The dry residue is subjected to chromatographic separation on 40 g of aluminum oxide.
When developing the chromatogram with absolute chloroform, only traces of yellow by-products go into the filtrate, while the iodineergotamine, which does not glow in UV light, is first washed into the filtrate with a mixture of chloroform with 1/2% alcohol.
It is eluted with this solvent until the zone, which adheres somewhat more strongly to the column and which is intensely purple in UV light, is about to be washed into the filtrate as well. The 260 mg of iodine-ergotamine obtained in this way crystallize from 90% strength acetone in straight cut plates, which melt at 1740 C with severe decomposition and contain crystal solvents.
[a121 of the product dried in a high vacuum at 1000 -156o (in chloroform).
EMI0001.0048
Kellersche <SEP> color reaction: <SEP> like <SEP> ergotamine.
<tb> Gross formula: <SEP> <B> C "H34väNGJl. </B>
<tb> ber .: <SEP> C <SEP> 55.99 <SEP> H <SEP> 4.85 <SEP> N <SEP> 9.90%
<tb> found: <SEP> 56.29 <SEP> 5.41 <SEP> 9.92%
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH263279T | 1947-07-22 | ||
| CH269043T | 1948-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH269043A true CH269043A (en) | 1950-06-15 |
Family
ID=25730624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH269043D CH269043A (en) | 1947-07-22 | 1948-04-29 | Process for the preparation of a derivative of the lysergic acid series halogenated on the indole nitrogen. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH269043A (en) |
-
1948
- 1948-04-29 CH CH269043D patent/CH269043A/en unknown
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