DK141963B - Fremgangsmåde til isolering af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen fra en isomer blanding, der består af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen og 3-cis-dimethylamino-4-phenyl-4-cis-carbethoxy-delta1-cyclohexen. - Google Patents
Fremgangsmåde til isolering af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen fra en isomer blanding, der består af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen og 3-cis-dimethylamino-4-phenyl-4-cis-carbethoxy-delta1-cyclohexen. Download PDFInfo
- Publication number
- DK141963B DK141963B DK559469AA DK559469A DK141963B DK 141963 B DK141963 B DK 141963B DK 559469A A DK559469A A DK 559469AA DK 559469 A DK559469 A DK 559469A DK 141963 B DK141963 B DK 141963B
- Authority
- DK
- Denmark
- Prior art keywords
- trans
- phenyl
- dimethylamino
- cyclohexene
- carbethoxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 33
- 238000000034 method Methods 0.000 title description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 41
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 24
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- 235000006408 oxalic acid Nutrition 0.000 description 10
- 239000001530 fumaric acid Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000012458 free base Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYVAVFURKHCMTG-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-phenylpropanoate Chemical compound CCOC(=O)C(CN(C)C)C1=CC=CC=C1 WYVAVFURKHCMTG-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229940032007 methylethyl ketone Drugs 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical class [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical group CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK259675A DK259675A (en, 2012) | 1969-04-17 | 1975-06-10 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81717669A | 1969-04-17 | 1969-04-17 | |
| US81717669 | 1969-04-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141963B true DK141963B (da) | 1980-07-28 |
| DK141963C DK141963C (en, 2012) | 1980-12-08 |
Family
ID=25222506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK559469AA DK141963B (da) | 1969-04-17 | 1969-10-22 | Fremgangsmåde til isolering af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen fra en isomer blanding, der består af 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-delta1-cyclohexen og 3-cis-dimethylamino-4-phenyl-4-cis-carbethoxy-delta1-cyclohexen. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3679732A (en, 2012) |
| JP (1) | JPS4948426B1 (en, 2012) |
| BE (1) | BE740072A (en, 2012) |
| BR (1) | BR6913399D0 (en, 2012) |
| CH (1) | CH514545A (en, 2012) |
| DK (1) | DK141963B (en, 2012) |
| ES (2) | ES372773A1 (en, 2012) |
| FR (1) | FR2039228A1 (en, 2012) |
| GB (1) | GB1226318A (en, 2012) |
| NL (1) | NL6915970A (en, 2012) |
| NO (1) | NO128655B (en, 2012) |
| SE (2) | SE375764B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978109A (en) * | 1970-02-17 | 1976-08-31 | Warner-Lambert Company | Process for substituted cyclohexenes |
| US4008233A (en) * | 1972-02-15 | 1977-02-15 | Warner-Lambert Company | Process for the preparation of 4r-amino-1t-phenyl-1c-ethoxycarbonyl-cyclohexenes-(2) |
| US3882164A (en) * | 1972-06-26 | 1975-05-06 | Warner Lambert Co | Dextrorotatory 3r-n-monomethyl-amino-4c-phenyl-4t-ethoxycarbonicyclohexene-1 and process for the production thereof |
| DE1000013T1 (de) * | 1997-07-14 | 2000-08-31 | Russinsky Ltd., Cork | Verfahren zur isomerisierung von tilidin |
| DE19902590A1 (de) * | 1999-01-22 | 2000-07-27 | Knoll Ag | Verfahren zur Reduktion des an 3-Dimethylamino-2-phenylpropionsäureethylester-Gehalts in Lösungen von 2-Dimethylamino-1-phenyl-3-cyclohexen-1-carbonsäureehtylester |
| WO2017021445A1 (en) * | 2015-08-06 | 2017-02-09 | Siegfried Pharmachemikalien Minden Gmbh | Tilidine isomerization and crystallization process |
-
1969
- 1969-04-17 US US817176A patent/US3679732A/en not_active Expired - Lifetime
- 1969-10-01 GB GB1226318D patent/GB1226318A/en not_active Expired
- 1969-10-09 FR FR6934612A patent/FR2039228A1/fr not_active Withdrawn
- 1969-10-10 BE BE740072D patent/BE740072A/xx unknown
- 1969-10-13 CH CH1531469A patent/CH514545A/fr not_active IP Right Cessation
- 1969-10-17 BR BR213399/69A patent/BR6913399D0/pt unknown
- 1969-10-22 SE SE7212424A patent/SE375764B/xx unknown
- 1969-10-22 ES ES372773A patent/ES372773A1/es not_active Expired
- 1969-10-22 NL NL6915970A patent/NL6915970A/xx unknown
- 1969-10-22 NO NO04201/69A patent/NO128655B/no unknown
- 1969-10-22 DK DK559469AA patent/DK141963B/da not_active IP Right Cessation
- 1969-10-22 SE SE14503/69A patent/SE365793B/xx unknown
- 1969-10-23 JP JP44084243A patent/JPS4948426B1/ja active Pending
-
1971
- 1971-12-09 ES ES397794A patent/ES397794A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4948426B1 (en, 2012) | 1974-12-21 |
| GB1226318A (en, 2012) | 1971-03-24 |
| NL6915970A (en, 2012) | 1970-10-20 |
| BR6913399D0 (pt) | 1973-01-04 |
| SE375764B (en, 2012) | 1975-04-28 |
| ES397794A1 (es) | 1974-05-16 |
| CH514545A (fr) | 1971-10-31 |
| SE365793B (en, 2012) | 1974-04-01 |
| ES372773A1 (es) | 1971-11-16 |
| FR2039228A1 (en, 2012) | 1971-01-15 |
| BE740072A (en, 2012) | 1970-04-10 |
| US3679732A (en) | 1972-07-25 |
| NO128655B (en, 2012) | 1973-12-27 |
| DK141963C (en, 2012) | 1980-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |