AT70786B - Process for the preparation of a hydrogenation product of colchicine. - Google Patents
Process for the preparation of a hydrogenation product of colchicine.Info
- Publication number
- AT70786B AT70786B AT70786DA AT70786B AT 70786 B AT70786 B AT 70786B AT 70786D A AT70786D A AT 70786DA AT 70786 B AT70786 B AT 70786B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- colchicine
- soluble
- preparation
- hydrogenation product
- Prior art date
Links
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 title claims description 11
- 229960001338 colchicine Drugs 0.000 title claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 238000001556 precipitation Methods 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Manufacture And Refinement Of Metals (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
EMI1.2
EMI1.3
<tb>
<tb>
<tb> Reagens <SEP> Colchicin <SEP> Tetrahydrocolchrein
<tb> Wasser <SEP> kalt <SEP> leicht <SEP> heiss <SEP> schwer <SEP> kalt <SEP> ziemlich <SEP> schwer. <SEP> heiss
<tb> löslich <SEP> schwer <SEP> löslich
<tb> Alkohol <SEP> sehr <SEP> leicht <SEP> löslich <SEP> sehr <SEP> leicht <SEP> löslich
<tb> Äther <SEP> sehr <SEP> schwer <SEP> loslich <SEP> ziemlich <SEP> löslich
<tb> Chloroform <SEP> sehr <SEP> leicht <SEP> löslich <SEP> sehr <SEP> leicht <SEP> loslich
<tb> benzol <SEP> leicht <SEP> loslich: <SEP> Ather <SEP> fällt <SEP> leicht <SEP> löslich:
<SEP> Äther <SEP> fallt
<tb> viel <SEP> wenig
<tb> Konzentrierte <SEP> Salpetersäure <SEP> violett. <SEP> dann <SEP> gelb <SEP> violett. <SEP> augenblicklieh
<tb> farblos
<tb> Konzentrierte <SEP> Schwefelsäure <SEP> gell <SEP> hellbraun, <SEP> nach <SEP> 24 <SEP> Stunden
<tb> weinrot
<tb> Konzentrterte <SEP> Schwefalsaure <SEP> und <SEP> grun. <SEP> blan. <SEP> dann <SEP> violett <SEP> braun. <SEP> dann <SEP> braunrot
<tb> Spur <SEP> Salpetertersaure <SEP> und <SEP> weinrot
<tb> Verdünnte <SEP> und <SEP> konzentrierte <SEP> gelh <SEP> farblos
<tb> SchwffelsäQrp. <SEP> i
<tb> Eisenchlorid <SEP> beim <SEP> Kochen <SEP> grün <SEP> auch <SEP> beim <SEP> Kochen <SEP> farblos
<tb> Quecksilberchlorid <SEP> und <SEP> gelber <SEP> Niederschlag <SEP> weisse.
<SEP> flockige <SEP> Fällung
<tb> Chloroform
<tb> Platinchlorid <SEP> keine <SEP> Fallung <SEP> keine <SEP> Fallung
<tb> Pikrinsäure <SEP> keine <SEP> Fällung <SEP> schwache <SEP> Trübung
<tb> Mayers <SEP> Reagens <SEP> keine <SEP> Fällung <SEP> keine <SEP> Fällung
<tb> Mayers <SEP> Reagens <SEP> und <SEP> Salzsäure <SEP> schöne <SEP> gelbe <SEP> Fällung <SEP> weisse <SEP> Fällung
<tb>
EMI1.4
<Desc/Clms Page number 2>
B e i s p i e l: 4 Teile amerphes Colchicin werden in 100 Teilen Wasser und 100 Teilen Alkohol gelöst und mit einer wässerigen Lösung von 0'1 Teil kolloidalem Palladium versetzt. In die von Luft befreite Flüssigkeit wird bei gelindem Überdruck Wasserstoff eingeleitet. Die Absorption beginnt sofort und ist bald beendigt. Um das Hydriertmgsprodukt abzuscheiden, wird der Alkohol im Vakuum verjagt und der zurückbleibenden wässerigen Lösung das hydrierte Colchicin durch Chloroform entzogen. Durch Verdampfen des Lösungsmittels und Trocknen im Vakuum erhält man das Hydrierungsprodukt als amorphe, spröde, fast farblose Masse, die gegen 1000 schmilzt.
Die Analyse ergab :
EMI2.1
<tb>
<tb> Berechnet <SEP> für <SEP> Gefunden:
<tb> C22H23NO4 <SEP> I <SEP> II <SEP> III <SEP> IV
<tb> C <SEP> = <SEP> 65.50% <SEP> 64.46% <SEP> - <SEP> - <SEP> H <SEP> = <SEP> 7.25% <SEP> 7.24% <SEP> - <SEP> - <SEP> N <SEP> = <SEP> 3.47% <SEP> - <SEP> 3.61% <SEP> - <SEP> OCH3 <SEP> = <SEP> 30.78% <SEP> - <SEP> - <SEP> 30.20% <SEP> 30.87%
<tb>
<Desc / Clms Page number 1>
EMI1.1
EMI1.2
EMI1.3
<tb>
<tb>
<tb> Reagent <SEP> Colchicine <SEP> Tetrahydrocolchrein
<tb> water <SEP> cold <SEP> light <SEP> hot <SEP> difficult <SEP> cold <SEP> fairly <SEP> difficult. <SEP> hot
<tb> soluble <SEP> poorly <SEP> soluble
<tb> Alcohol <SEP> very <SEP> slightly <SEP> soluble <SEP> very <SEP> slightly <SEP> soluble
<tb> ether <SEP> very <SEP> difficult <SEP> soluble <SEP> fairly <SEP> soluble
<tb> Chloroform <SEP> very <SEP> slightly <SEP> soluble <SEP> very <SEP> slightly <SEP> soluble
<tb> benzene <SEP> slightly <SEP> soluble: <SEP> ether <SEP> drops <SEP> easily <SEP> soluble:
<SEP> ether <SEP> falls
<tb> a lot <SEP> little
<tb> Concentrated <SEP> nitric acid <SEP> violet. <SEP> then <SEP> yellow <SEP> violet. <SEP> instantly
<tb> colorless
<tb> Concentrated <SEP> sulfuric acid <SEP> gell <SEP> light brown, <SEP> after <SEP> 24 <SEP> hours
<tb> wine red
<tb> Concentrated <SEP> sulfuric acid <SEP> and <SEP> green. <SEP> blan. <SEP> then <SEP> violet <SEP> brown. <SEP> then <SEP> brown-red
<tb> trace <SEP> nitric acid <SEP> and <SEP> wine red
<tb> Diluted <SEP> and <SEP> concentrated <SEP> gelh <SEP> colorless
<tb> SchwffelsäQrp. <SEP> i
<tb> Ferric chloride <SEP> when <SEP> boiling <SEP> green <SEP> also <SEP> when <SEP> boiling <SEP> colorless
<tb> mercury chloride <SEP> and <SEP> yellow <SEP> precipitate <SEP> white.
<SEP> flaky <SEP> precipitation
<tb> chloroform
<tb> platinum chloride <SEP> no <SEP> precipitation <SEP> no <SEP> precipitation
<tb> Picric acid <SEP> no <SEP> precipitation <SEP> weak <SEP> turbidity
<tb> Mayer's <SEP> reagent <SEP> no <SEP> precipitation <SEP> no <SEP> precipitation
<tb> Mayer's <SEP> reagent <SEP> and <SEP> hydrochloric acid <SEP> beautiful <SEP> yellow <SEP> precipitation <SEP> white <SEP> precipitation
<tb>
EMI1.4
<Desc / Clms Page number 2>
Example: 4 parts of amorphous colchicine are dissolved in 100 parts of water and 100 parts of alcohol, and an aqueous solution of 0.1 part of colloidal palladium is added. Hydrogen is introduced into the air-removed liquid at a slight excess pressure. The absorption begins immediately and is soon completed. In order to separate out the hydrogenation product, the alcohol is driven off in vacuo and the hydrogenated colchicine is removed from the remaining aqueous solution by chloroform. By evaporating the solvent and drying in vacuo, the hydrogenation product is obtained as an amorphous, brittle, almost colorless mass that melts towards 1000
The analysis showed:
EMI2.1
<tb>
<tb> Calculates <SEP> for <SEP> Found:
<tb> C22H23NO4 <SEP> I <SEP> II <SEP> III <SEP> IV
<tb> C <SEP> = <SEP> 65.50% <SEP> 64.46% <SEP> - <SEP> - <SEP> H <SEP> = <SEP> 7.25% <SEP> 7.24% <SEP> - <SEP > - <SEP> N <SEP> = <SEP> 3.47% <SEP> - <SEP> 3.61% <SEP> - <SEP> OCH3 <SEP> = <SEP> 30.78% <SEP> - <SEP> - < SEP> 30.20% <SEP> 30.87%
<tb>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE70786X | 1913-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT70786B true AT70786B (en) | 1915-12-27 |
Family
ID=5635571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT70786D AT70786B (en) | 1913-06-09 | 1914-04-30 | Process for the preparation of a hydrogenation product of colchicine. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT70786B (en) |
-
1914
- 1914-04-30 AT AT70786D patent/AT70786B/en active
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