DE222920C - - Google Patents
Info
- Publication number
- DE222920C DE222920C DENDAT222920D DE222920DA DE222920C DE 222920 C DE222920 C DE 222920C DE NDAT222920 D DENDAT222920 D DE NDAT222920D DE 222920D A DE222920D A DE 222920DA DE 222920 C DE222920 C DE 222920C
- Authority
- DE
- Germany
- Prior art keywords
- morphine
- formic acid
- parts
- water
- formylcodeine
- 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.)
- Active
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class 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 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 229930013053 morphinan alkaloid Natural products 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 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 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229960004126 codeine Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- OHDRXVUBUAODDQ-DNJOTXNNSA-N [(4r,4ar,7s,7ar,12bs)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-yl] formate Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC=O OHDRXVUBUAODDQ-DNJOTXNNSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VSGXFWNZWWGPCT-ZLLBLOTGSA-N (4r,4ar,5s,7as,12bs)-5-chloro-3-methyl-2,4,4a,5,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-ol Chemical compound O([C@H]1C=C[C@H](Cl)[C@H]23)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O VSGXFWNZWWGPCT-ZLLBLOTGSA-N 0.000 description 1
- CYNZTGLNKBWNHM-SCGCMHLBSA-N (4r,4ar,7as,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=CC[C@@H]1OC1=C2C3=CC=C1OC CYNZTGLNKBWNHM-SCGCMHLBSA-N 0.000 description 1
- OJHWKGLOJHIELT-ZFDIKFDDSA-N (4r,4ar,7s,7ar,12bs)-7-bromo-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-ol Chemical compound O([C@H]1[C@H](C=C[C@H]23)Br)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O OJHWKGLOJHIELT-ZFDIKFDDSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- -1 morphine ethers Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE233325T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE222920C true DE222920C (enrdf_load_stackoverflow) |
Family
ID=32997311
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT233325D Active DE233325C (enrdf_load_stackoverflow) | |||
| DENDAT229246D Active DE229246C (enrdf_load_stackoverflow) | |||
| DENDAT222920D Active DE222920C (enrdf_load_stackoverflow) |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT233325D Active DE233325C (enrdf_load_stackoverflow) | |||
| DENDAT229246D Active DE229246C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (3) | DE222920C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT233325D patent/DE233325C/de active Active
- DE DENDAT229246D patent/DE229246C/de active Active
- DE DENDAT222920D patent/DE222920C/de active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DE233325C (enrdf_load_stackoverflow) | |
| DE229246C (enrdf_load_stackoverflow) |
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