DE301139C - - Google Patents
Info
- Publication number
- DE301139C DE301139C DENDAT301139D DE301139DA DE301139C DE 301139 C DE301139 C DE 301139C DE NDAT301139 D DENDAT301139 D DE NDAT301139D DE 301139D A DE301139D A DE 301139DA DE 301139 C DE301139 C DE 301139C
- Authority
- DE
- Germany
- Prior art keywords
- ether
- hydrochloric acid
- percent
- ester
- anhydronorecgonine
- 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
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical class O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 150000002832 nitroso derivatives Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- UFUIYOBDFZLHCY-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C(=O)OCCCBr)C=C1 Chemical compound [N+](=O)([O-])C1=CC=C(C(=O)OCCCBr)C=C1 UFUIYOBDFZLHCY-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229960003920 cocaine Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- SOWYHPBNCZZWRP-UHFFFAOYSA-N 1-hydroxypropyl benzoate Chemical compound CCC(O)OC(=O)C1=CC=CC=C1 SOWYHPBNCZZWRP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- YNQKCHQJQNRNHW-UHFFFAOYSA-N ethyl 8-methyl-8-azabicyclo[3.2.1]oct-3-ene-4-carboxylate Chemical compound CCOC(=O)C1=CCC2CCC1N2C YNQKCHQJQNRNHW-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 2
- SOYUXANHDDRWAO-UHFFFAOYSA-N 3-bromopropyl benzoate Chemical compound BrCCCOC(=O)C1=CC=CC=C1 SOYUXANHDDRWAO-UHFFFAOYSA-N 0.000 description 1
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UFLMJULGUPSTCY-UHFFFAOYSA-M sodium;4-nitrobenzoate Chemical compound [Na+].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 UFLMJULGUPSTCY-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE301139C true DE301139C (enrdf_load_stackoverflow) |
Family
ID=555059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT301139D Active DE301139C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE301139C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT301139D patent/DE301139C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1468092B2 (de) | Aminopropoxy-derivate des tetrahydronaphthalins und des indans, deren saeureadditionssalze, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate | |
| DE1227447B (de) | Verfahren zur Herstellung von Phenylisopropylaminen | |
| DE301139C (enrdf_load_stackoverflow) | ||
| DE945391C (de) | Verfahren zur Herstellung von Bicycloheptyl- bzw. Bicycloheptenylaminen | |
| DE1210806B (de) | Verfahren zur Herstellung von sekundaeren Alkyl- oder Alkylenaminen oder deren nicht toxischen Salzen | |
| DE296916C (enrdf_load_stackoverflow) | ||
| DE116806C (enrdf_load_stackoverflow) | ||
| DE364038C (de) | Verfahren zur Darstellung von ª‡-Dialkylaminoaethyl-ª‰-aracidyloxybuttersaeureestern | |
| DE1795003C3 (de) | 4H-13-Benzoxazin-2-on-3-acetohydroxamsäure, Verfahren zu deren Herstellung und Arzneimittel | |
| DE194051C (enrdf_load_stackoverflow) | ||
| DE181287C (enrdf_load_stackoverflow) | ||
| DE2265632C2 (de) | Verfahren zur Herstellung von 2,4,6,8-Tetramethyl-2,4,6,8-tetraazabicyclo-[3,3,0]-octandion-(3,7) | |
| DE1618632C (de) | Verfahren zur Herstellung von trans 4-Phenylcyclohexylamin Salzen von alpha (4 Biphenyl) alkansauren mit entzundungs hemmenden und schmerzlindernden Eigen schäften | |
| DE1620172C (de) | Optisch aktives oder racemisches 2,3-Dimethoxy-10-aminoberbin, dessen Salze und Verfahren zur Herstellung dieser Verbindung | |
| AT214910B (de) | Verfahren zur Herstellung von neuen, am Stickstoffatom und am β-Kohlenstoffatom substituierten Buttersäureamiden | |
| DE854526C (de) | Verfahren zur Herstellung von Aminoalkoholen | |
| DE87812C (enrdf_load_stackoverflow) | ||
| DE200203C (enrdf_load_stackoverflow) | ||
| DD155296A1 (de) | Verfahren zur extraktion von kupfer aus waessrigen loesungen | |
| DE1518311C (de) | N (2 Diathylaminoathyl) 2 methoxy 3,4 bzw 4,5 methylendioxybenzamid und deren pharmakologisch nicht giftige Saureadditions salze | |
| DE1545543B1 (de) | 4-Aminobutinylimide,ihre Salze und Verfahren zu deren Herstellung | |
| DE937232C (de) | Verfahren zur Herstellung von Salzen der Penicilline mit p-Amino-o-chlorbenzoesaeure-diaethylaminoaethylester | |
| DE1768787C3 (de) | (o-Carboxy-phenyl)-acetamidine, Verfahren zu deren Herstellung und (o-CarboxyphenyO-acetamidine enthaltende Präparate | |
| AT215972B (de) | Verfahren zur Herstellung von neuen, eine Dreifachbindung enthaltenden ungradzahligen Fettsäuren und deren Salzen | |
| AT92388B (de) | Verfahren zur Darstellung von Aralkylestern der Benzylamincarbonsäuren. |