DE39887C - Process for the preparation of methylmorphine (codeine and ethylmorphine - Google Patents
Process for the preparation of methylmorphine (codeine and ethylmorphineInfo
- Publication number
- DE39887C DE39887C DENDAT39887D DE39887DA DE39887C DE 39887 C DE39887 C DE 39887C DE NDAT39887 D DENDAT39887 D DE NDAT39887D DE 39887D A DE39887D A DE 39887DA DE 39887 C DE39887 C DE 39887C
- Authority
- DE
- Germany
- Prior art keywords
- morphine
- codeine
- methylmorphine
- ethylmorphine
- preparation
- 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 - Lifetime
Links
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 title claims description 4
- 229960004578 Ethylmorphine Drugs 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
- 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 title description 8
- 229960004126 codeine Drugs 0.000 title description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N Morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 11
- 229930014694 morphine Natural products 0.000 claims description 11
- 229960005181 morphine Drugs 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 4
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl sulfate Chemical class CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-N Methyl bisulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims description 2
- ZENNIHDHUIWZRA-SEJAZBPASA-N (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC ZENNIHDHUIWZRA-SEJAZBPASA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- -1 Ethyl codeine Chemical compound 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 229930013930 alkaloids Natural products 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Chemical group 0.000 description 1
- 239000002184 metal Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005429 turbidity Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12:.^Chemische Apparate und Processe.CLASS 12:. ^ Chemical Apparatus and Processes.
&'J '■' vf& 'J' ■ 'vf
Patentirt im Deutschen Reiche vom 7. August 1886 ab.Patented in the German Empire on August 7, 1886.
Das neue Verfahren zur Darstellung von Methyl- und Aethylmorphin beruht auf Erwärmung von Morphin bezw. Morphinalkali oder Morphinerdalkali mit methyl- und äthylschwefelsauren Salzen, wobei das Alkyl der letzteren in das Morphinmolecül an Stelle eines Wasserstoff- oder des Metallatoms eintritt. Diese Umsetzung unter Bildung von Methylbezw. Aethylcodein erfolgt sowohl in wässeriger, als auch alkoholischer Lösung und beim Arbeiten unter Druck, wie auch ohne Druck.The new process for the preparation of methyl and ethyl morphine is based on heating of morphine resp. Morphine alkali or morphine earth alkali with methyl and ethylsulphuric acid salts, the alkyl of the the latter enters the morphine molecule in place of a hydrogen or metal atom. This reaction with the formation of Methylbezw. Ethyl codeine occurs both in aqueous, as well as alcoholic solution and when working under pressure as well as without pressure.
Um das Methylmorphin oder Codein darzustellen, löse man 1 Theil Morphin in zwei Theilen von cjoprocentigem Alkohol unter Zusatz von so viel Kali- oder Natronlauge, dafs alles Morphin in Lösung geht, versetze diese Lösung mit methylschwefelsaurem Kali oder Natron in berechneter oder überschüssiger Menge und koche 2 Stunden am Rückflufskühler im Wasserbade, wobei die Code'inbildung sich unter Bräunung und Trübung der Flüssigkeit vollzieht.To prepare methylmorphine or codeine, dissolve 1 part of morphine in two Part of cjoprocent alcohol with added add so much potassium hydroxide or sodium hydroxide solution that all morphine goes into solution, add it Solution with methylsulfuric acid potash or soda in calculated or excess Quantity and boil for 2 hours on the reflux condenser in a water bath, whereby the code'in formation takes place with browning and turbidity of the liquid.
Die Abscheidung des Codems und die Wiedergewinnung von unzersetztem Morphin erfolgt nach bekannten Verfahren, z. B. durch Neutralisiren mit Schwefelsäure, Befreien von Alkohol, Verdünnen mit Wasser, Fällen des Morphins mit Ammoniak und Abfiltriren, Ausschütteln des Code'ins mit Benzol und weitere Isolirung und Reinigung, wie bei Alkaloiden allgemein üblich.The separation of the codeme and the recovery of undecomposed morphine takes place according to known methods, e.g. B. by neutralizing with sulfuric acid, freeing Alcohol, dilution with water, precipitation of the morphine with ammonia and filtering off, shaking out of the code'ins with benzene and further isolation and purification, as with alkaloids common practice.
In ganz analoger Weise verfahre man bei Darstellung von Aethylmorphin.Proceed in a completely analogous manner when preparing ethylmorphine.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE39887C true DE39887C (en) |
Family
ID=315482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT39887D Expired - Lifetime DE39887C (en) | Process for the preparation of methylmorphine (codeine and ethylmorphine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE39887C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949645B1 (en) | 2004-05-20 | 2005-09-27 | Acura Pharmaceuticals, Inc. | Process for the production of opiates |
| US6972332B1 (en) | 2004-05-20 | 2005-12-06 | Acura Pharmaceuticals, Inc. | Process for the production of opiates |
-
0
- DE DENDAT39887D patent/DE39887C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949645B1 (en) | 2004-05-20 | 2005-09-27 | Acura Pharmaceuticals, Inc. | Process for the production of opiates |
| US6972332B1 (en) | 2004-05-20 | 2005-12-06 | Acura Pharmaceuticals, Inc. | Process for the production of opiates |
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