DE1238040B - Verfahren zur Herstellung von 4H-Benzo [4, 5]-cyclohepta [1, 2-b] thiophenen - Google Patents
Verfahren zur Herstellung von 4H-Benzo [4, 5]-cyclohepta [1, 2-b] thiophenenInfo
- Publication number
- DE1238040B DE1238040B DES95277A DES0095277A DE1238040B DE 1238040 B DE1238040 B DE 1238040B DE S95277 A DES95277 A DE S95277A DE S0095277 A DES0095277 A DE S0095277A DE 1238040 B DE1238040 B DE 1238040B
- Authority
- DE
- Germany
- Prior art keywords
- benzo
- cyclohepta
- solution
- ecm
- propylidene
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 4
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 title description 3
- -1 chloroformic acid ester Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- AZLFZBHRVLSJRH-UHFFFAOYSA-N N,N-dimethyl-3-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ylidene)propan-1-amine Chemical class CN(CCC=C1C2=C(C=CC=3SC=CC31)C=CC=C2)C AZLFZBHRVLSJRH-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- ISSJZCAENPGUEW-BQYQJAHWSA-N 2-[(e)-2-thiophen-2-ylethenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1\C=C\C1=CC=CS1 ISSJZCAENPGUEW-BQYQJAHWSA-N 0.000 description 4
- JAGBUENUSNSSFW-UHFFFAOYSA-N 4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=C1SC=C2 JAGBUENUSNSSFW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- BYSDXOIAAYZTBJ-UHFFFAOYSA-N 2-(2-thiophen-2-ylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CS1 BYSDXOIAAYZTBJ-UHFFFAOYSA-N 0.000 description 2
- NFHHBIGYIAIGFH-UHFFFAOYSA-N 2h-cyclohepta[b]thiophene Chemical compound C1=CC=CC2=CCSC2=C1 NFHHBIGYIAIGFH-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- MLNVBGMXAUTXPQ-UHFFFAOYSA-N N-methyl-3-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ylidene)propan-1-amine Chemical compound CNCCC=C1C2=C(C=CC=3SC=CC31)C=CC=C2 MLNVBGMXAUTXPQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229940054441 o-phthalaldehyde Drugs 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- ZDYPMKZEUSYJQI-LZYBPNLTSA-N (3e)-3-(4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-ylidene)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(=C/CCN(C)C)\C2=C1SC=C2 ZDYPMKZEUSYJQI-LZYBPNLTSA-N 0.000 description 1
- SKEKJIUZLXYWCM-UHFFFAOYSA-N 13-chloro-2-[3-(dimethylamino)propyl]-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,11,13-pentaen-2-ol Chemical compound ClC=1C=CC2=C(C(C3=C(SC=C3)CC2)(O)CCCN(C)C)C1 SKEKJIUZLXYWCM-UHFFFAOYSA-N 0.000 description 1
- CFVZFYUQERHDOE-UHFFFAOYSA-N 13-chloro-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,8,11,13-hexaen-2-one Chemical compound O=C1C2=CC(Cl)=CC=C2C=CC2=C1C=CS2 CFVZFYUQERHDOE-UHFFFAOYSA-N 0.000 description 1
- URGQYBULFKLFMX-UHFFFAOYSA-N 2-chloro-6-formylbenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1C=O URGQYBULFKLFMX-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MMTTWQAQUZDXSB-UHFFFAOYSA-N 2H-cyclohepta[b]thiophen-4-ol Chemical compound S1C=2C(=CC1)C(=CC=CC2)O MMTTWQAQUZDXSB-UHFFFAOYSA-N 0.000 description 1
- RDBMZAMQBNYOIJ-UHFFFAOYSA-N 3-(4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-ylidene)-n-methylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=C1SC=C2 RDBMZAMQBNYOIJ-UHFFFAOYSA-N 0.000 description 1
- HAYRVPQPKWWYDQ-UHFFFAOYSA-N 5-chloro-2-(2-thiophen-2-ylethenyl)benzoic acid Chemical compound OC(=O)C1=C(C=CC2=CC=CS2)C=CC(Cl)=C1 HAYRVPQPKWWYDQ-UHFFFAOYSA-N 0.000 description 1
- OFZLWQHTSQPJLX-UHFFFAOYSA-N 5-chloro-2-(2-thiophen-2-ylethyl)benzoic acid Chemical compound ClC=1C=CC(=C(C(=O)O)C1)CCC=1SC=CC1 OFZLWQHTSQPJLX-UHFFFAOYSA-N 0.000 description 1
- NQAMSLASTWZONN-UHFFFAOYSA-N 5-chloro-2-formylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1C=O NQAMSLASTWZONN-UHFFFAOYSA-N 0.000 description 1
- XBSHFWJFRSEMTE-UHFFFAOYSA-N 6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ol Chemical compound S1C2=C(C=C1)C(C1=C(C=C2)C=CC=C1)O XBSHFWJFRSEMTE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUMHIOPSVXZEST-UHFFFAOYSA-N 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,7a-hexahydrobenzo[a]quinolizin-2-one Chemical compound C1CN2CC(CC(C)C)C(=O)CC2=C2C1C=C(OC)C(OC)=C2 GUMHIOPSVXZEST-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- LMBHNMKBUKHVGQ-UHFFFAOYSA-N CCOC(NC(C)CC=C1C(C=CC=C2)=C2C=CC2=C1C=CS2)=O Chemical compound CCOC(NC(C)CC=C1C(C=CC=C2)=C2C=CC2=C1C=CS2)=O LMBHNMKBUKHVGQ-UHFFFAOYSA-N 0.000 description 1
- LHARTHCFXKDMSZ-UHFFFAOYSA-N CN(CCCC1(C2=C(CCC=3SC=CC31)C=CC=C2)O)C Chemical compound CN(CCCC1(C2=C(CCC=3SC=CC31)C=CC=C2)O)C LHARTHCFXKDMSZ-UHFFFAOYSA-N 0.000 description 1
- NTGDRLLWKDTZRA-UHFFFAOYSA-N CN(CCCC1C2=C(CCC=3SC=CC31)C=CC=C2)C Chemical compound CN(CCCC1C2=C(CCC=3SC=CC31)C=CC=C2)C NTGDRLLWKDTZRA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- AKYJPOPHGMQXHH-UHFFFAOYSA-N benzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=C1SC=C2 AKYJPOPHGMQXHH-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- MWWHYPORGYMFIP-UHFFFAOYSA-N cyclohepta[b]thiophen-4-one Chemical compound O=C1C=CC=CC2=C1C=CS2 MWWHYPORGYMFIP-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- HSBVGAFLCXUIMZ-UHFFFAOYSA-N ethyl N-[4-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene)butan-2-yl]carbamate Chemical compound CC(CC=C1C2=C(CCC=3SC=CC=31)C=CC=C2)NC(=O)OCC HSBVGAFLCXUIMZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH127564A CH440321A (de) | 1964-02-04 | 1964-02-04 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| CH1324664 | 1964-10-13 | ||
| CH806165A CH473138A (de) | 1964-02-04 | 1965-06-09 | Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten |
| CH1519165A CH473146A (de) | 1964-02-04 | 1965-11-03 | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1238040B true DE1238040B (de) | 1967-04-06 |
Family
ID=27428140
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES95277A Pending DE1238040B (de) | 1964-02-04 | 1965-02-01 | Verfahren zur Herstellung von 4H-Benzo [4, 5]-cyclohepta [1, 2-b] thiophenen |
| DE19661620420 Pending DE1620420A1 (de) | 1964-02-04 | 1966-10-28 | Neue 4H-Benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620420 Pending DE1620420A1 (de) | 1964-02-04 | 1966-10-28 | Neue 4H-Benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate |
Country Status (12)
| Country | Link |
|---|---|
| BE (2) | BE659178A (en, 2012) |
| BR (2) | BR6566936D0 (en, 2012) |
| CH (2) | CH473138A (en, 2012) |
| DE (2) | DE1238040B (en, 2012) |
| ES (1) | ES332985A2 (en, 2012) |
| FI (1) | FI42216B (en, 2012) |
| FR (4) | FR1441486A (en, 2012) |
| GB (2) | GB1089483A (en, 2012) |
| IL (1) | IL22905A (en, 2012) |
| NL (2) | NL125442C (en, 2012) |
| OA (1) | OA01524A (en, 2012) |
| SE (1) | SE306323B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195800B (en) * | 1983-10-13 | 1988-07-28 | Sandoz Ltd | Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them |
| JP5116928B2 (ja) | 1999-09-13 | 2013-01-09 | ブリッジ ファーマ、インコーポレイテッド | ケトチフェン及びその治療上有効な代謝産物の光学活性異性体 |
-
1965
- 1965-01-26 GB GB3355/65A patent/GB1089483A/en not_active Expired
- 1965-01-28 OA OA51413A patent/OA01524A/xx unknown
- 1965-01-29 NL NL6501154A patent/NL125442C/xx active
- 1965-02-01 DE DES95277A patent/DE1238040B/de active Pending
- 1965-02-02 FI FI0244/65A patent/FI42216B/fi active
- 1965-02-02 BE BE659178A patent/BE659178A/xx unknown
- 1965-02-02 FR FR4164A patent/FR1441486A/fr not_active Expired
- 1965-02-03 SE SE1405/65A patent/SE306323B/xx unknown
- 1965-02-03 IL IL22905A patent/IL22905A/en unknown
- 1965-02-04 BR BR166936/65A patent/BR6566936D0/pt unknown
- 1965-04-30 FR FR15304A patent/FR4369M/fr not_active Expired
- 1965-06-09 CH CH806165A patent/CH473138A/de unknown
- 1965-08-09 NL NL6510326A patent/NL6510326A/xx unknown
- 1965-08-09 BE BE668052A patent/BE668052A/xx unknown
- 1965-08-10 FR FR27925A patent/FR91208E/fr not_active Expired
- 1965-11-03 CH CH1519165A patent/CH473146A/de unknown
-
1966
- 1966-10-21 GB GB47266/66A patent/GB1159480A/en not_active Expired
- 1966-10-28 DE DE19661620420 patent/DE1620420A1/de active Pending
- 1966-10-31 BR BR184229/66A patent/BR6684229D0/pt unknown
- 1966-11-02 ES ES332985A patent/ES332985A2/es not_active Expired
- 1966-11-02 FR FR82202A patent/FR92121E/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6566936D0 (pt) | 1973-08-14 |
| OA01524A (fr) | 1969-07-21 |
| CH473138A (de) | 1969-05-31 |
| NL6510326A (en, 2012) | 1966-12-12 |
| FR4369M (en, 2012) | 1966-08-22 |
| FI42216B (en, 2012) | 1970-03-02 |
| CH473146A (de) | 1969-05-31 |
| GB1089483A (en) | 1967-11-01 |
| IL22905A (en) | 1969-01-29 |
| FR1441486A (fr) | 1966-06-10 |
| NL125442C (en, 2012) | 1968-06-17 |
| BE659178A (en, 2012) | 1965-08-02 |
| FR91208E (fr) | 1968-05-03 |
| BR6684229D0 (pt) | 1973-12-26 |
| SE306323B (en, 2012) | 1968-11-25 |
| GB1159480A (en) | 1969-07-23 |
| FR92121E (fr) | 1968-09-27 |
| BE668052A (en, 2012) | 1966-02-09 |
| DE1620420A1 (de) | 1970-03-12 |
| ES332985A2 (es) | 1968-03-16 |
| NL6501154A (en, 2012) | 1965-08-05 |
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