DE937229C - Verfahren zur Herstellung bestimmter Isomeren von 1-(4-Bromphenyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) und von 1-(5-Chlor-2-thienyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) - Google Patents
Verfahren zur Herstellung bestimmter Isomeren von 1-(4-Bromphenyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) und von 1-(5-Chlor-2-thienyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1)Info
- Publication number
- DE937229C DE937229C DEW6589A DEW0006589A DE937229C DE 937229 C DE937229 C DE 937229C DE W6589 A DEW6589 A DE W6589A DE W0006589 A DEW0006589 A DE W0006589A DE 937229 C DE937229 C DE 937229C
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- pyrrolidino
- bromophenyl
- chloro
- propen
- 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
Links
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 title claims description 13
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- -1 1- (5-chloro-2-thienyl) -1- (2- pyridyl) -3-pyrrolidino-propene Chemical compound 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000000862 absorption spectrum Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000031700 light absorption Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical class CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SRXJYTZCORKVNA-UHFFFAOYSA-N 1-bromoethenylbenzene Chemical group BrC(=C)C1=CC=CC=C1 SRXJYTZCORKVNA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB293570X | 1950-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE937229C true DE937229C (de) | 1955-12-29 |
Family
ID=10290229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEW6589A Expired DE937229C (de) | 1950-08-29 | 1951-08-26 | Verfahren zur Herstellung bestimmter Isomeren von 1-(4-Bromphenyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) und von 1-(5-Chlor-2-thienyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE505509A (en, 2012) |
| CH (1) | CH293570A (en, 2012) |
| DE (1) | DE937229C (en, 2012) |
| FR (1) | FR1055958A (en, 2012) |
| GB (1) | GB701445A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
-
0
- BE BE505509D patent/BE505509A/xx unknown
-
1950
- 1950-08-29 GB GB21354/50A patent/GB701445A/en not_active Expired
-
1951
- 1951-08-26 DE DEW6589A patent/DE937229C/de not_active Expired
- 1951-08-29 CH CH293570D patent/CH293570A/fr unknown
- 1951-08-29 FR FR1055958D patent/FR1055958A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
Also Published As
| Publication number | Publication date |
|---|---|
| BE505509A (en, 2012) | |
| FR1055958A (fr) | 1954-02-23 |
| CH293570A (fr) | 1953-09-30 |
| GB701445A (en) | 1953-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH661045A5 (de) | Wasserfreie, stabile kristalline form von prazosinhydrochlorid und verfahren zu dessen herstellung. | |
| DE1695753B2 (de) | Verfahren zur Herstellung von 6,6disubstituierten 2,2-Dimethyl-4-oxopiperidinen | |
| DE3419947A1 (de) | "3-(3-hydroxybutoxy)-1-butanol, verfahren zu seiner herstellung und diese verbindung enthaltende arzneimittel | |
| DE2902466A1 (de) | Optisch aktiver substituierter benzylalkohol und dessen herstellungsverfahren | |
| DE2547540A1 (de) | Verfahren zur herstellung von hydroxypivaldehyd | |
| DE2651500A1 (de) | Di(phenoxy-2 alkancarbonsaeuren), verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| DE1518517C (en, 2012) | ||
| DE1493971C3 (de) | Verfahren zur Gewinnung einer Phenolfraktion mit vermindertem Gehalt an alpha Hydroxycarbonyl verbindungen | |
| DE937229C (de) | Verfahren zur Herstellung bestimmter Isomeren von 1-(4-Bromphenyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) und von 1-(5-Chlor-2-thienyl)-1-(2-pyridyl)-3-pyrrolidino-propen-(1) | |
| DE1227464B (de) | Verfahren zur Herstellung der trans-Form des neuen 1-(4'-Methylphenyl)-1-(2''-pyridyl)-3-pyrrolidinopropens-(1) | |
| DE2058519C3 (de) | Verfahren zur Gewinnung von Ditrimethylolpropan aus einem dasselbe enthaltende Reaktionsgemisch | |
| DE1618502A1 (de) | Verfahren zur Herstellung von Polyenverbindungen | |
| DE1493323B2 (de) | 1-(p-hydroxyphenyl)-2-phenyl-6methoxy- 3,4-dihydronaphthalin, dessen pharmakologisch geeignete salze und verfahren zur herstellung dieser verbindungen | |
| DE2045668C3 (de) | Verfahren zur Gewinnung von reinem 2,2-Dimethylpropandiol-(l,3) | |
| DE1939695C3 (de) | Gewinnung von d-Xylose aus Sulfitlauge von Hartholz mit Hilfe von azeotropischem Isopropylalkohol | |
| DE2145517B1 (de) | Verfahren zur abtrennung von formaldehyd unter gewinnung reiner essigsaeure aus gemischen von essigsaeure, formeldehyd und wasser | |
| DE1963824B2 (de) | 3-Benzylphenylessigsäurederivate, Verfahren zu ihrer Herstellung und Verwendung zur Herstellung von Derivaten der 2-(3-Benzoyl-2-hydroxyphenyl)-essigsäure | |
| DE1468283C (en, 2012) | ||
| AT137322B (de) | Verfahren zum Konzentrieren wässeriger Ameisensäure. | |
| DE844894C (de) | Verfahren zur Gewinnung konzentrierter Buttersaeure | |
| DE3212069A1 (de) | Verfahren zur herstellung von o-nitrobenzaldehyd | |
| AT261109B (de) | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae | |
| US3165556A (en) | Preparation of divinyl and tetravinyl ethers of pentaerythritol | |
| CH495309A (de) | Verfahren zur Herstellung von Dihydromyrcenol | |
| AT282629B (de) | Verfahren zur herstellung neuer zimtsaeureamide |