CH111996A - Method for the preparation of codeinone. - Google Patents
Method for the preparation of codeinone.Info
- Publication number
- CH111996A CH111996A CH111996DA CH111996A CH 111996 A CH111996 A CH 111996A CH 111996D A CH111996D A CH 111996DA CH 111996 A CH111996 A CH 111996A
- Authority
- CH
- Switzerland
- Prior art keywords
- codeinone
- preparation
- solution
- weakly acidic
- acidic solution
- Prior art date
Links
- XYYVYLMBEZUESM-CMKMFDCUSA-N codeinone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=CC(=O)[C@@H]1OC1=C2C3=CC=C1OC XYYVYLMBEZUESM-CMKMFDCUSA-N 0.000 title claims description 7
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HGPQAWTZLJXCTC-SSTWWWIQSA-N (4r,4ar,7s,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical compound C([C@@H](N(CC1)C)[C@@H]2C=C[C@@H]3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 HGPQAWTZLJXCTC-SSTWWWIQSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 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)
Description
Verfahren zur Darstellung von Iiodelnon. Gemäss Patent Nr. 111121 erhält man Kodeinon aus Kodein durch Oxydation in schwach saurer Lösung. Auch ist Kodeinon aus Thebain (dem Methyläther der Enolform des Kodeinons) durch Hydrolyse in schwefel saurer Lösung erhalten worden (vergl. Berichte, 39/190G, Seite 1409 u. ff.).
EMI0001.0012
Es wurde nun -gefunden, dass man Kodeinon auch in der Weise erhalten kann, wenn man das gemäss Patent Nr.
111995 herstellbare Methylkodein
EMI0001.0016
in schwach saurer Lösung oxydiert. <I>Beispiel:</I> 4 gr Methylkodein werden in 5 em3 zirka 20 /oiger Essigsäure gelöst und unter Kühlung mit einer Lösung von 4 gr Chromsäure in 5 cm' Wasser versetzt, wobei ein Chromat ausfiel, das jedoch unter Ansteigen der Tem peratur auf 40-50 o in Lösung ging. Hier auf wurde stark abgekühlt, wobei Kristalli sation eines Chromates eintrat, das nach seiner Isolierung mit Ammoniak zerlegt wurde. Die Base mit Äther aufgenommen.
Beim Ab destillieren desselben kristallisierte eine Ver- bindung, die als Kodeinon identifiziert werden konnte.
Procedure for the representation of iiodelnon. According to patent no. 111121, codeinone is obtained from codeine by oxidation in a weakly acidic solution. Codeinone has also been obtained from thebaine (the methyl ether of the enol form of codeinone) by hydrolysis in a sulfuric acid solution (see reports, 39 / 190G, page 1409 and ff.).
EMI0001.0012
It has now been found that codeinone can also be obtained in the same way if the according to patent no.
111995 producible methylcodeine
EMI0001.0016
oxidized in weakly acidic solution. <I> Example: </I> 4 g of methylcodeine are dissolved in 5 em3 of about 20% acetic acid and, while cooling, a solution of 4 g of chromic acid in 5 cm 'of water is added, a chromate precipitating which, however, as the temp increases temperature to 40-50 o went into solution. This was strongly cooled, with crystallization of a chromate occurred, which was broken down with ammonia after its isolation. The base was added with ether.
When it was distilled off, a compound crystallized which could be identified as codeinone.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE111996X | 1923-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH111996A true CH111996A (en) | 1925-10-01 |
Family
ID=5652745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH111996D CH111996A (en) | 1923-10-18 | 1924-07-30 | Method for the preparation of codeinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH111996A (en) |
-
1924
- 1924-07-30 CH CH111996D patent/CH111996A/en unknown
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