DE3000888A1 - Verfahren zur herstellung von 5-(2-chlorbenzyl)-4,5,6,7- tetrahydrothieno eckige klammer auf 3,2-c eckige klammer zu pyridin - Google Patents
Verfahren zur herstellung von 5-(2-chlorbenzyl)-4,5,6,7- tetrahydrothieno eckige klammer auf 3,2-c eckige klammer zu pyridinInfo
- Publication number
- DE3000888A1 DE3000888A1 DE19803000888 DE3000888A DE3000888A1 DE 3000888 A1 DE3000888 A1 DE 3000888A1 DE 19803000888 DE19803000888 DE 19803000888 DE 3000888 A DE3000888 A DE 3000888A DE 3000888 A1 DE3000888 A1 DE 3000888A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorobenzyl
- pyridine
- reaction
- raney nickel
- iii
- 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.)
- Granted
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 7
- -1 2-CHLORBENZYL Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 239000007868 Raney catalyst Substances 0.000 claims description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19831/79A IT1166580B (it) | 1979-02-02 | 1979-02-02 | Processo per la preparazione dell 5-(2-clorobenzil)-4,5,6,7-tetraidrotieno(3,2-c)piridina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3000888A1 true DE3000888A1 (de) | 1980-08-07 |
| DE3000888C2 DE3000888C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-11-17 |
Family
ID=11161641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803000888 Granted DE3000888A1 (de) | 1979-02-02 | 1980-01-11 | Verfahren zur herstellung von 5-(2-chlorbenzyl)-4,5,6,7- tetrahydrothieno eckige klammer auf 3,2-c eckige klammer zu pyridin |
Country Status (8)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6185391A (ja) * | 1984-10-03 | 1986-04-30 | Nisshin Flour Milling Co Ltd | ５−（２−クロロベンジル）−４，５，６，７−テトラヒドロチエノ〔３，２−ｃ〕ピリジンの製造方法 |
| EP0573975A1 (en) * | 1992-06-08 | 1993-12-15 | Fuji Photo Film Co., Ltd. | 2-alkoxycarbonyl-5-o-chlorobenzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine derivative and process for producing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2404308B2 (de) * | 1973-02-01 | 1977-06-30 | Centre d'Etudes pour !'Industrie Pharmaceutique, Toulouse (Frankreich) | Thieno bzw. furo eckige klammer auf 3,2-c eckige klammer zu pyridiniumderivate sowie deren 4,5,6,7-tetrahydroderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
-
1979
- 1979-02-02 IT IT19831/79A patent/IT1166580B/it active
-
1980
- 1980-01-11 DE DE19803000888 patent/DE3000888A1/de active Granted
- 1980-01-23 FR FR8001440A patent/FR2447923A1/fr active Granted
- 1980-01-24 AT AT0036880A patent/AT372089B/de not_active IP Right Cessation
- 1980-01-25 ES ES488694A patent/ES8102130A1/es not_active Expired
- 1980-01-28 BE BE2/58368A patent/BE881360A/fr not_active IP Right Cessation
- 1980-01-30 AR AR279806A patent/AR222686A1/es active
- 1980-02-01 PT PT70767A patent/PT70767A/pt unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2404308B2 (de) * | 1973-02-01 | 1977-06-30 | Centre d'Etudes pour !'Industrie Pharmaceutique, Toulouse (Frankreich) | Thieno bzw. furo eckige klammer auf 3,2-c eckige klammer zu pyridiniumderivate sowie deren 4,5,6,7-tetrahydroderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| AT372089B (de) | 1983-08-25 |
| PT70767A (en) | 1980-03-01 |
| AR222686A1 (es) | 1981-06-15 |
| ES488694A0 (es) | 1980-12-16 |
| DE3000888C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-11-17 |
| FR2447923A1 (fr) | 1980-08-29 |
| FR2447923B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-06-24 |
| IT1166580B (it) | 1987-05-05 |
| BE881360A (fr) | 1980-05-16 |
| IT7919831A0 (it) | 1979-02-02 |
| ES8102130A1 (es) | 1980-12-16 |
| ATA36880A (de) | 1983-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |