CH450397A - Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-10,11-dihydrocycloheptenen - Google Patents
Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-10,11-dihydrocycloheptenenInfo
- Publication number
- CH450397A CH450397A CH736163A CH736163A CH450397A CH 450397 A CH450397 A CH 450397A CH 736163 A CH736163 A CH 736163A CH 736163 A CH736163 A CH 736163A CH 450397 A CH450397 A CH 450397A
- Authority
- CH
- Switzerland
- Prior art keywords
- dibenzo
- hydrogen
- hydrogenated
- compounds
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- -1 aminopropylidene compounds Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- BBTGWJWEBLBVAQ-UHFFFAOYSA-N tricyclo[9.4.0.01,6]pentadeca-2,4,6,8,11,13-hexaene Chemical compound C1C=CC=C2C13C(=CC=CC2)C=CC=C3 BBTGWJWEBLBVAQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202721A US3205264A (en) | 1962-06-15 | 1962-06-15 | Process for the preparation of 10, 11-dihydro-5-(gamma-methyl-and dimethyl-amino propylidene)-5h-dibenzo[a, d] cycloheptene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH450397A true CH450397A (de) | 1968-01-31 |
Family
ID=22750985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH736163A CH450397A (de) | 1962-06-15 | 1963-06-13 | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-10,11-dihydrocycloheptenen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3205264A (en, 2012) |
| BR (1) | BR6349682D0 (en, 2012) |
| CH (1) | CH450397A (en, 2012) |
| GB (1) | GB1049064A (en, 2012) |
| SE (1) | SE327698B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK114828B (da) * | 1962-11-29 | 1969-08-11 | Hoffmann La Roche | Fremgangsmåde til fremstilling af 5-hydroxy-5-aminoalkyl-10,11-dihydro-5H-dibenzo-(a,d)-cykloheptener eller syreadditionssalte deraf. |
| US6197830B1 (en) * | 1995-09-22 | 2001-03-06 | Bruce M. Frome | Method for achieving relief from sympathetically mediated pain |
| TW200400816A (en) * | 2002-06-26 | 2004-01-16 | Lilly Co Eli | Tricyclic steroid hormone nuclear receptor modulators |
| CN102657664A (zh) | 2003-09-12 | 2012-09-12 | 阿勒根公司 | 用于治疗疼痛和其它α2肾上腺素能介导疾病的方法及组合物 |
| ZA200804550B (en) | 2005-11-09 | 2009-08-26 | Combinatorx Inc | Methods, compositions, and kits for the treatment of medical conditions |
| JP5643103B2 (ja) | 2007-11-28 | 2014-12-17 | ウェルズ ファーゴ バンク ナショナル アソシエイション | オリゴマー−三環物質コンジュゲート |
| WO2011091050A1 (en) | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| WO2012079017A1 (en) | 2010-12-10 | 2012-06-14 | Nektar Therapeutics | Hydroxylated tricyclic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB858188A (en) * | 1953-04-03 | 1961-01-11 | Hoffmann La Roche | Novel dibenzocycloheptaenes and salts thereof and a process for the manufacture of same |
| US3073847A (en) * | 1959-02-12 | 1963-01-15 | Hoffmann La Roche | 9-(3-amino-1-propynyl) derivatives of 9-xanthenols and 9-thioxanthenols and a process for their preparation |
-
1962
- 1962-06-15 US US202721A patent/US3205264A/en not_active Expired - Lifetime
-
1963
- 1963-04-14 SE SE06635/63*A patent/SE327698B/xx unknown
- 1963-05-29 GB GB21483/63A patent/GB1049064A/en not_active Expired
- 1963-06-05 BR BR149682/63A patent/BR6349682D0/pt unknown
- 1963-06-13 CH CH736163A patent/CH450397A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1049064A (en) | 1966-11-23 |
| US3205264A (en) | 1965-09-07 |
| SE327698B (en, 2012) | 1970-08-31 |
| BR6349682D0 (pt) | 1973-07-12 |
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