SU562196A3 - Способ получени производных декагидроизохинолина - Google Patents

Способ получени производных декагидроизохинолина

Info

Publication number: SU562196A3
Authority: SU; USSR - Soviet Union
Prior art keywords: diketo; phenyl; formula; trans; decahydroisoquinoline
Prior art date: 1972-07-20

Application number

SU1951133A

Other languages

English (en)

Russian (ru)

Inventor

Росс Бриттелли Дэвид

Чарльз Рипка Вильям

Original Assignee

Е.И.Дюпон Де Немур Энд Компани (Фирма)

Priority date (The priority date 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 date listed.)

1972-07-20

Filing date

1973-07-19

Publication date

1977-06-15

1973-07-19 Application filed by Е.И.Дюпон Де Немур Энд Компани (Фирма) filed Critical Е.И.Дюпон Де Немур Энд Компани (Фирма)

1977-06-15 Application granted granted Critical

1977-06-15 Publication of SU562196A3 publication Critical patent/SU562196A3/ru

Links

238000000034 method Methods 0.000 title description 6
NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical class C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 title 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
-1 lithium aluminum hydride Chemical compound 0.000 claims description 12
238000010992 reflux Methods 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
229910000104 sodium hydride Inorganic materials 0.000 claims description 9
239000012280 lithium aluminium hydride Substances 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000012312 sodium hydride Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
239000000047 product Substances 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
239000000203 mixture Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000706 filtrate Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
235000010446 mineral oil Nutrition 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
150000003949 imides Chemical class 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZVUPIZCQKCQXCR-HOTGVXAUSA-N (4ar,8ar)-2-methyl-4a-phenyl-1,3,4,5,6,7,8,8a-octahydroisoquinoline Chemical compound C1([C@]23CCN(C[C@@H]2CCCC3)C)=CC=CC=C1 ZVUPIZCQKCQXCR-HOTGVXAUSA-N 0.000 description 2
AYKOCNRDYSODOJ-BBRMVZONSA-N (4ar,8ar)-2-methyl-4a-phenyl-4,5,6,7,8,8a-hexahydroisoquinoline-1,3-dione Chemical compound C1([C@]23CC(=O)N(C([C@@H]2CCCC3)=O)C)=CC=CC=C1 AYKOCNRDYSODOJ-BBRMVZONSA-N 0.000 description 2
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
FLHFTXCMKFVKRP-UHFFFAOYSA-N bromomethylcyclobutane Chemical compound BrCC1CCC1 FLHFTXCMKFVKRP-UHFFFAOYSA-N 0.000 description 2
AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
239000003245 coal Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
NENLYAQPNATJSU-IUCAKERBSA-N (4as,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCC[C@@H]2CCCC[C@H]21 NENLYAQPNATJSU-IUCAKERBSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
ATDSLTNNQHIUGT-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4a-phenyl-4,5,6,7-tetrahydroisoquinoline-1,3-dione Chemical compound O=C1CC2(C=3C=CC=CC=3)CCCC=C2C(=O)N1CC1CCCCC1 ATDSLTNNQHIUGT-UHFFFAOYSA-N 0.000 description 1
MDCSEDZSJXOKHT-UHFFFAOYSA-N 2-methyl-4a-phenyl-4,5,6,7-tetrahydroisoquinoline-1,3-dione Chemical compound C1CCC=C2C(=O)N(C)C(=O)CC21C1=CC=CC=C1 MDCSEDZSJXOKHT-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
RIYGJSDIJWHXJS-UHFFFAOYSA-N 4-[4-(9-hydroxynonoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 RIYGJSDIJWHXJS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LBQAGPTYGDCVSC-PMACEKPBSA-N C1(CCC1)CN1C[C@@H]2CCCC[C@]2(CC1)C1=CC=CC=C1 Chemical compound C1(CCC1)CN1C[C@@H]2CCCC[C@]2(CC1)C1=CC=CC=C1 LBQAGPTYGDCVSC-PMACEKPBSA-N 0.000 description 1
DFHUCZVFFSAETP-UGKGYDQZSA-N C1(CCCCC1)CN1C([C@@H]2CCCC[C@]2(CC1=O)C1=CC=CC=C1)=O Chemical compound C1(CCCCC1)CN1C([C@@H]2CCCC[C@]2(CC1=O)C1=CC=CC=C1)=O DFHUCZVFFSAETP-UGKGYDQZSA-N 0.000 description 1
FSVPKHBCGLKONR-NKWVEPMBSA-N C1CCC[C@H]2C(=O)NC(=O)C[C@@H]21 Chemical compound C1CCC[C@H]2C(=O)NC(=O)C[C@@H]21 FSVPKHBCGLKONR-NKWVEPMBSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
229910010082 LiAlH Inorganic materials 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
239000000908 ammonium hydroxide Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
ZKFYDQGUPNCXLY-UHFFFAOYSA-N ethyl 2-(2-cyanocyclohex-2-en-1-yl)acetate Chemical class CCOC(=O)CC1CCCC=C1C#N ZKFYDQGUPNCXLY-UHFFFAOYSA-N 0.000 description 1
CVHSSGQGPQJKGJ-UHFFFAOYSA-N ethyl 2-[2-cyano-1-(3-methoxyphenyl)cyclohex-2-en-1-yl]acetate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCC=C1C#N CVHSSGQGPQJKGJ-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
RUNIEFCRNHEYJO-UHFFFAOYSA-N oxolane;sodium Chemical compound [Na].C1CCOC1 RUNIEFCRNHEYJO-UHFFFAOYSA-N 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

SU1951133A 1972-07-20 1973-07-19 Способ получени производных декагидроизохинолина SU562196A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US27380672A	1972-07-20	1972-07-20

Publications (1)

Publication Number	Publication Date
SU562196A3 true SU562196A3 (ru)	1977-06-15

Family

ID=23045484

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1951133A SU562196A3 (ru)	1972-07-20	1973-07-19	Способ получени производных декагидроизохинолина
SU7502114526A SU574153A3 (ru)	1972-07-20	1975-03-18	Способ получени 1,3-дикетооктагидроизохинолинов

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU7502114526A SU574153A3 (ru)	1972-07-20	1975-03-18	Способ получени 1,3-дикетооктагидроизохинолинов

Country Status (4)

Country	Link
AT (1)	AT330179B (fr)
BE (1)	BE802557A (fr)
SU (2)	SU562196A3 (fr)
ZA (1)	ZA734895B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4208524A (en) *	1974-05-07	1980-06-17	Eli Lilly And Company	N-Alkenyl decahydroisoquinolines
US4001248A (en) *	1974-06-07	1977-01-04	Eli Lilly And Company	N-cycloalkylmethyl decahydroisoquinolines
US4001247A (en) *	1974-06-07	1977-01-04	Eli Lilly And Company	1-ethyl 3a-(substituted-phenyl) decahydroisoquinoline
SE7509022L (sv) *	1974-09-09	1976-03-10	Du Pont	Foreningar med analgetisk verkan
US4219652A (en) *	1975-09-30	1980-08-26	Eli Lilly And Company	N-Methyl and N-phenethyl-cis-decahydroisoquinolines
US4077954A (en) *	1976-02-10	1978-03-07	E. I. Du Pont De Nemours And Company	N-(p-methylphenethyl)-4a-aryl-trans-decahydroisoquinolines
US4141893A (en) *	1976-11-02	1979-02-27	Eli Lilly And Company	Decahydrocyclopent[c]azepines
US4337341A (en)	1976-11-02	1982-06-29	Eli Lilly And Company	4a-Aryl-octahydro-1H-2-pyrindines
US4141894A (en) *	1976-11-02	1979-02-27	Eli Lilly And Company	Trans-5a-aryl-decahydrobenzazepines
BG30927A3 (bg) *	1977-12-27	1981-09-15	Eli Lilly And Company	Метод за получаване на транс-4-алфа-фенил-октахидро-1н-2 пиридини
US4289882A (en) *	1978-04-26	1981-09-15	The United States Of America As Represented By The Department Of Health & Human Services	4A-Aryl-decahydroisoquinolines
US4236009A (en) *	1979-06-21	1980-11-25	Eli Lilly And Company	Method of preparing 4A-arylhexahydro-1H-2-pyrindines and 4A-aryloctahydroisoquinolines
US4277608A (en) *	1979-06-21	1981-07-07	Eli Lilly And Company	Method of preparing 4a-arylhexahydro-1H-2-pyrindines and 4a-aryloctahydroisoquinolines

1973
- 1973-07-18 AT AT632873A patent/AT330179B/de not_active IP Right Cessation
- 1973-07-18 ZA ZA734895A patent/ZA734895B/xx unknown
- 1973-07-19 BE BE133657A patent/BE802557A/fr unknown
- 1973-07-19 SU SU1951133A patent/SU562196A3/ru active
1975
- 1975-03-18 SU SU7502114526A patent/SU574153A3/ru active

Also Published As

Publication number	Publication date
AT330179B (de)	1976-06-25
BE802557A (fr)	1973-11-16
ZA734895B (en)	1974-06-26
ATA632873A (de)	1975-09-15
SU574153A3 (ru)	1977-09-25

Publication	Publication Date	Title
SU562196A3 (ru)	1977-06-15	Способ получени производных декагидроизохинолина
SU588916A3 (ru)	1978-01-15	Способ получени 2-тетрагидрофурил-6,7-бензоморфанов или их солей
SU552025A3 (ru)	1977-03-25	Способ получени производных фенил-имидазолил-алканов
JP2635213B2 (ja)	1997-07-30	化学工程
US2528267A (en)	1950-10-31	Eobeet j
EP0249610B1 (fr)	1993-08-25	Synthese d'aryloxypropanolamines et arylethanolamines optiquement actives
US3106564A (en)	1963-10-08	1-(2-phenoxy-2-phenylethyl) pyrrolidine
CA1118431A (fr)	1982-02-16	Procede de preparation d'un cis(.sup. -)-3, 4- dihydro-n,n,2-trimethyl-2h-1-benzopyran-3-amine et produits intermediaires
RU2070194C1 (ru)	1996-12-10	Способ получения производных гексагидроазепинов или их солей с минеральными или органическими кислотами
SU479290A3 (ru)	1975-07-30	Способ получени 2-(фурилметил)-6,7бензоморфанов
US5191112A (en)	1993-03-02	Process for optical resolution of (±)-2-(3-benzoyl)-phenylpropionic acid
US3978085A (en)	1976-08-31	Process for benz[f]-2,5-oxazocines
CS202044B2 (en)	1980-12-31	Method of preparation of 2-arylpropione acids
US3946012A (en)	1976-03-23	6-L-dihydroxyethyl-2,4,7-trioxo-8-D-ribityl pteridine and process for producing the same
SU564805A3 (ru)	1977-07-05	Способ получени производных -(3,3-дифенилпропил)пропилендиамина или их солей
US3637759A (en)	1972-01-25	Chromanes
US4188491A (en)	1980-02-12	Preparation of therapeutic compounds
CZ100895A3 (en)	1995-10-18	Enantiomeric cis-3-(4,6-dihydroxychroman-3-ylmethyl)benzoic acids
US3007940A (en)	1961-11-07	Method of preparing derivatives of 3, 3-pentamethylene-4-hydroxybutyric acid
US2893993A (en)	1959-07-07	2-aryloxyaralkyl-1, 4, 5, 6-tetrahydropyrimidines
US3058992A (en)	1962-10-16	Intermediates for the preparation of
US4021478A (en)	1977-05-03	Preparation of carboxylic acids from glycidonitriles with ionic lewis acids
US5395985A (en)	1995-03-07	Compound and separating agent
US3892771A (en)	1975-07-01	Substituted dihydroisoindoles
US3152129A (en)	1964-10-06	Triethylene diamine fumarate and its uses in recovery of diazabicyclooctane