CH481055A - Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten - Google Patents
Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-DerivatenInfo
- Publication number
- CH481055A CH481055A CH1716868A CH1716868A CH481055A CH 481055 A CH481055 A CH 481055A CH 1716868 A CH1716868 A CH 1716868A CH 1716868 A CH1716868 A CH 1716868A CH 481055 A CH481055 A CH 481055A
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- dibenzo
- aminomethylated
- dihydro
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical class C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CJDMGGVKOZCNJH-UHFFFAOYSA-N 1-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-n,n-dimethylmethanamine Chemical compound C1CC2=CC=CC=C2C(CN(C)C)C2=CC=CC=C21 CJDMGGVKOZCNJH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1716868A CH481055A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH678166A CH473759A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten |
| CH1716868A CH481055A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH481055A true CH481055A (de) | 1969-11-15 |
Family
ID=4314928
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1716868A CH481055A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten |
| CH1716968A CH481869A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten |
| CH678166A CH473759A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1716968A CH481869A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten |
| CH678166A CH473759A (de) | 1966-05-10 | 1966-05-10 | Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten |
Country Status (12)
| Country | Link |
|---|---|
| AT (3) | AT283303B (ref) |
| BE (1) | BE698198A (ref) |
| CH (3) | CH481055A (ref) |
| CS (4) | CS154229B2 (ref) |
| DE (1) | DE1643212A1 (ref) |
| ES (1) | ES340257A1 (ref) |
| FI (1) | FI47348C (ref) |
| FR (1) | FR6502M (ref) |
| GB (1) | GB1170798A (ref) |
| GR (1) | GR36291B (ref) |
| NL (1) | NL6706480A (ref) |
| NO (1) | NO122246B (ref) |
-
1966
- 1966-05-10 CH CH1716868A patent/CH481055A/de not_active IP Right Cessation
- 1966-05-10 CH CH1716968A patent/CH481869A/de not_active IP Right Cessation
- 1966-05-10 CH CH678166A patent/CH473759A/de not_active IP Right Cessation
-
1967
- 1967-05-03 FI FI671285A patent/FI47348C/fi active
- 1967-05-03 DE DE19671643212 patent/DE1643212A1/de active Pending
- 1967-05-05 GB GB20979/67A patent/GB1170798A/en not_active Expired
- 1967-05-08 GR GR670136291A patent/GR36291B/el unknown
- 1967-05-08 ES ES340257A patent/ES340257A1/es not_active Expired
- 1967-05-09 AT AT434967A patent/AT283303B/de not_active IP Right Cessation
- 1967-05-09 AT AT870569A patent/AT283311B/de not_active IP Right Cessation
- 1967-05-09 AT AT870769A patent/AT283312B/de not_active IP Right Cessation
- 1967-05-09 BE BE698198D patent/BE698198A/xx unknown
- 1967-05-09 NO NO168071A patent/NO122246B/no unknown
- 1967-05-09 NL NL6706480A patent/NL6706480A/xx unknown
- 1967-05-10 CS CS281170*1A patent/CS154229B2/cs unknown
- 1967-05-10 CS CS281270*1A patent/CS154230B2/cs unknown
- 1967-05-10 FR FR105888A patent/FR6502M/fr not_active Expired
- 1967-05-10 CS CS337867A patent/CS154228B2/cs unknown
- 1967-05-10 CS CS281370*1A patent/CS154231B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES340257A1 (es) | 1968-09-01 |
| CS154231B2 (ref) | 1974-03-29 |
| NL6706480A (ref) | 1967-11-13 |
| GR36291B (el) | 1969-01-20 |
| CH481869A (de) | 1969-11-30 |
| FI47348C (fi) | 1973-11-12 |
| DE1643212A1 (de) | 1971-03-11 |
| CS154228B2 (ref) | 1974-03-29 |
| CS154229B2 (ref) | 1974-03-29 |
| AT283312B (de) | 1970-08-10 |
| FR6502M (ref) | 1968-12-02 |
| FI47348B (ref) | 1973-07-31 |
| CS154230B2 (ref) | 1974-03-29 |
| BE698198A (ref) | 1967-11-09 |
| AT283303B (de) | 1970-08-10 |
| GB1170798A (en) | 1969-11-19 |
| CH473759A (de) | 1969-06-15 |
| NO122246B (ref) | 1971-06-07 |
| AT283311B (de) | 1970-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1518207B1 (de) | Verfahren zur Herstellung von neuen Phenylcyclopropanderivaten bzw. deren Salzen und quaternaeren Ammoniumverbindungen | |
| DE2413102A1 (de) | Verfahren zur herstellung von 1-(3,5dihydroxyphenyl)-1-hydroxy-2- eckige klammer auf 1-methyl-2-(4-hydroxyphenyl)-aethyl eckige klammer zu -amino-aethan | |
| CH373397A (de) | Verfahren zur Herstellung symmetrischer Diamine | |
| CH481055A (de) | Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten | |
| CH450397A (de) | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-10,11-dihydrocycloheptenen | |
| DE945449C (de) | Verfahren zur Herstellung von 2-Methyl-4-cyclohexyl-6-methyl-aminomethylphenol | |
| CH485654A (de) | Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-Derivaten | |
| CH520117A (de) | Verfahren zur Herstellung von basisch substituierten Oximen des 5H-Dibenzo-(a,d)-10,11-dihydro-cyclohepten-5-ons | |
| CH356121A (de) | Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren | |
| DE907650C (de) | Verfahren zur Herstellung von Iso-1, 2-Diaryl-aethanol-(1)-aminen-(2) | |
| DE1670019C3 (de) | N-Aminoalkenyl- und -alkinylsuccinimide und sie enthaltende MIttel | |
| AT162899B (de) | Verfahren zur Darstellung von neuen Aminoalkyläthern von Alkoholen der aromatischaliphatischen Reihe | |
| AT283306B (de) | Verfahren zur Herstellung von neuen 5-aminomethylierten 10,11-Dihydro-5H-dibenzo[a,d]-cycloheptenen und ihren Salzen | |
| DE939207C (de) | Verfahren zur Herstellung von als Lokalanaesthetica verwendbaren basisch substituierten Fettsaeure-(2-chlor-6-methyl-aniliden) und ihren Salzen | |
| CH513806A (de) | Verfahren zur Herstellung von tricyclischen Verbindungen | |
| AT206424B (de) | Verfahren zur Herstellung des neuen bis-γ-Chlorpropyl)-amins und dessen Salzen | |
| DE964056C (de) | Verfahren zur Herstellung von Thiophenderivaten | |
| DE477050C (de) | Verfahren zur Darstellung von hydrocyclischen ªÏ-Aminoalkylverbindungen | |
| DE1518207C (de) | Verfahren zur Herstellung von neuen Phenylcyclopropandenvaten bzw deren Salzen und quaternaren Ammomumverbin düngen | |
| DE967642C (de) | Verfahren zur Herstellung von basisch substituierten Buttersaeure-aniliden | |
| DE1443604C3 (de) | 1 -Aminomethyl-1,2-dihydro-benzocyclobuten und einige seiner Derivate, Salze dieser Verbindungen, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende pharmazeutische Präparate | |
| AT238186B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| AT239209B (de) | Verfahren zur Herstellung von neuen bicyclisch substituierten Aminoalkanen sowie deren Salzen und quaternären Ammoniumverbindungen | |
| AT210891B (de) | Verfahren zur Herstellung von neuen Methylpiperidylpentanol-estern | |
| DE1445638C (de) | 9 geschweifte Klammer auf gamma eckige Klammer auf N* (beta hydroxyaryl) piperazino eckige Klammer zu propyl geschweifte Klam mer zu 9,10 dihydro 9,10 athano (1,2) anthra zen und seme Salze, Verfahren zu deren Her stellung und pharmazeutisches Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |