DE623694C - - Google Patents
Info
- Publication number
- DE623694C DE623694C DENDAT623694D DE623694DA DE623694C DE 623694 C DE623694 C DE 623694C DE NDAT623694 D DENDAT623694 D DE NDAT623694D DE 623694D A DE623694D A DE 623694DA DE 623694 C DE623694 C DE 623694C
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- ether
- solution
- hours
- ecm
- 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
- 229930013930 alkaloid Natural products 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002730 mercury Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 235000001258 Cinchona calisaya Nutrition 0.000 description 8
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 8
- 229960000948 quinine Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- LJOQGZACKSYWCH-WZBLMQSHSA-N hydroquinine Chemical compound C1=C(OC)C=C2C([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-WZBLMQSHSA-N 0.000 description 4
- 229960004251 hydroquinine Drugs 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KZSGJHYBMKOXRP-UHFFFAOYSA-N Hydrocinchonidine Natural products OC(C1CC2CCN1CC2C=C)C3CC=Nc4ccccc34 KZSGJHYBMKOXRP-UHFFFAOYSA-N 0.000 description 3
- WFJNHVWTKZUUTR-QAMTZSDWSA-N Hydrocinchonine Chemical compound C1=CC=C2C([C@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 WFJNHVWTKZUUTR-QAMTZSDWSA-N 0.000 description 3
- WFJNHVWTKZUUTR-UHFFFAOYSA-N dihydrocinchonidine Natural products C1=CC=C2C(C(O)C3CC4CCN3CC4CC)=CC=NC2=C1 WFJNHVWTKZUUTR-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- XUPFNPFFFUXGMP-UHFFFAOYSA-N isoindole-1,3-dione;silver Chemical compound [Ag].C1=CC=C2C(=O)NC(=O)C2=C1 XUPFNPFFFUXGMP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE623694C true DE623694C (enrdf_load_stackoverflow) |
Family
ID=576652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT623694D Active DE623694C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE623694C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7649094B2 (en) * | 2002-01-31 | 2010-01-19 | Daiso Co., Ltd. | Optically active compounds, method for kinetic optical resolution of carboxylic acid derivatives and catalysts therefor |
-
0
- DE DENDAT623694D patent/DE623694C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7649094B2 (en) * | 2002-01-31 | 2010-01-19 | Daiso Co., Ltd. | Optically active compounds, method for kinetic optical resolution of carboxylic acid derivatives and catalysts therefor |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE623694C (enrdf_load_stackoverflow) | ||
| DE1182671B (de) | Verfahren zur Herstellung von neuen AEthern und Thioaethern des Panthenols | |
| DE2449492A1 (de) | Verfahren zur herstellung von optisch aktivem p-hydroxyphenylglycin | |
| DE2751901A1 (de) | Herstellungsverfahren fuer am stickstoff substituierte imide | |
| DE102007053947A1 (de) | Verfahren zur Synthese von Saccharose-6-Essigsäureester | |
| EP0028758B1 (de) | Verfahren zur Herstellung von Pivaloylbrenztraubensäurealkylestern und -cycloalkylestern | |
| DE2234997A1 (de) | Verfahren zur herstellung von cycloalkenonestern | |
| DE563259C (de) | Verfahren zur Darstellung von basischen Abkoemmlingen des Guajacols | |
| DE890189C (de) | Verfahren zur Herstellung von Barbitursaeureabkoemmlingen | |
| DE2264903C3 (de) | Piperidinderivate und ihre Herstellung | |
| DE1242603B (de) | Verfahren zur Herstellung von 5-Hydroxy-5-aminoalkyl-di-benzo-[a, d]-cycloheptanen | |
| DE1236521B (de) | Verfahren zur Herstellung von substituierten 1-Thia-2-sila-cyclopentanen | |
| DE280225C (enrdf_load_stackoverflow) | ||
| DE2651939C2 (de) | Verfahren zur Herstellung von Succinylobernsteinsäurediestern | |
| DE662646C (de) | Verfahren zur Darstellung von Oxyzimtsaeuren | |
| DE3307614A1 (de) | Verfahren zur herstellung von 1-decyloxy-4-((7-oxa-4-octinyl)-oxy)-benzol | |
| DE248737C (enrdf_load_stackoverflow) | ||
| DE946986C (de) | Verfahren zur Herstellung von ª‡-Acetotetronsaeuren | |
| DE2127260C3 (de) | D-(-)- alpha -azidophenylessigsaures (-) - alpha -Phenyläthylamin, seine Herstellung und Verwendung | |
| DE1090225B (de) | Verfahren zur Herstellung von p-Nitrodiphenylaminen | |
| DE671840C (de) | Verfahren zur Herstellung cyclischer Arylaether | |
| DE279197C (enrdf_load_stackoverflow) | ||
| DE960721C (de) | Verfahren zur Herstellung von 2, 5-substituierten 2, 5-Dihydrofuranderivaten | |
| DE3134106A1 (de) | Verfahren zur trennung des racemats s-(carboxymethyl)-(r,s)-cystein (b) | |
| DE2656604A1 (de) | Verfahren zur herstellung von 1-(2-tetrahydrofuryl)-5-fluoruracil |