SU643084A3 - Способ получени 8-бензофурилметил-1,3,8триазаспиро /4,5/деканов - Google Patents
Способ получени 8-бензофурилметил-1,3,8триазаспиро /4,5/декановInfo
- Publication number
- SU643084A3 SU643084A3 SU731945861A SU1945861A SU643084A3 SU 643084 A3 SU643084 A3 SU 643084A3 SU 731945861 A SU731945861 A SU 731945861A SU 1945861 A SU1945861 A SU 1945861A SU 643084 A3 SU643084 A3 SU 643084A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazaspiro
- decane
- oxo
- dihydro
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- -1 lithium aluminum hydride Chemical compound 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- HTQWGIHCFPWKAS-UHFFFAOYSA-N 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CNCCC11C(=O)NCN1C1=CC=CC=C1 HTQWGIHCFPWKAS-UHFFFAOYSA-N 0.000 description 1
- OPAYERWEZXLSFC-UHFFFAOYSA-N 5-methoxy-1-benzofuran-2-carbaldehyde Chemical compound COC1=CC=C2OC(C=O)=CC2=C1 OPAYERWEZXLSFC-UHFFFAOYSA-N 0.000 description 1
- OWIQMDBGEZTQNU-UHFFFAOYSA-N 8-[(5-fluoro-2,3-dihydro-1-benzofuran-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1(=CC=CC=C1)N1CNC(C12CCN(CC2)CC2OC1=C(C2)C=C(C=C1)F)=O OWIQMDBGEZTQNU-UHFFFAOYSA-N 0.000 description 1
- VDQCWRRMOBTXRC-UHFFFAOYSA-N 8-[(5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound O=C1NCNC12CCN(CC2)CC2OC1=C(C2)C=C(C=C1)OC VDQCWRRMOBTXRC-UHFFFAOYSA-N 0.000 description 1
- AYTHWHPHHWUZSP-UHFFFAOYSA-N 8-[(5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-methyl-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(NC2(C1=O)CCN(CC2)CC2OC1=C(C2)C=C(C=C1)OC)=O AYTHWHPHHWUZSP-UHFFFAOYSA-N 0.000 description 1
- ZBWRKPVACXNZIW-UHFFFAOYSA-N 8-[(5-methoxy-3-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1(=CC=CC=C1)N1CNC(C11CCN(CC1)CC1OC2=C(C1C)C=C(C=C2)OC)=O ZBWRKPVACXNZIW-UHFFFAOYSA-N 0.000 description 1
- RJPQJZUMKGSBGG-UHFFFAOYSA-N 8-[(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1(=CC=CC=C1)N1CNC(C12CCN(CC2)CC2OC1=C(C2)C=CC=C1OC)=O RJPQJZUMKGSBGG-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- TUEGTJJPOCFEKS-UHFFFAOYSA-N COC1=CC2=C(CC(O2)CN3CCC4(CC3)C(=O)NCN4C5=CC=CC=C5)C=C1 Chemical compound COC1=CC2=C(CC(O2)CN3CCC4(CC3)C(=O)NCN4C5=CC=CC=C5)C=C1 TUEGTJJPOCFEKS-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Confectionery (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10512671A | 1971-01-08 | 1971-01-08 | |
| US00183694A US3826835A (en) | 1971-01-08 | 1971-09-24 | 8-benzofurylmethyl-1,3,8-triazaspiro(4,5)decanes as neuroleptics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU643084A3 true SU643084A3 (ru) | 1979-01-15 |
Family
ID=26802278
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731945861A SU643084A3 (ru) | 1971-01-08 | 1973-07-10 | Способ получени 8-бензофурилметил-1,3,8триазаспиро /4,5/деканов |
| SU1945862A SU520046A3 (ru) | 1971-01-08 | 1973-07-10 | Способ получени 8-(1(2,3-дигидро-2-бензофурил) -алкил)-1,3,8-триазаспиро (4,5)деканов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1945862A SU520046A3 (ru) | 1971-01-08 | 1973-07-10 | Способ получени 8-(1(2,3-дигидро-2-бензофурил) -алкил)-1,3,8-триазаспиро (4,5)деканов |
Country Status (10)
| Country | Link |
|---|---|
| AR (3) | AR192608A1 (cg-RX-API-DMAC7.html) |
| CS (3) | CS166798B2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES398670A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI53315C (cg-RX-API-DMAC7.html) |
| HU (1) | HU166687B (cg-RX-API-DMAC7.html) |
| IE (1) | IE35926B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL38439A (cg-RX-API-DMAC7.html) |
| NO (1) | NO133229C (cg-RX-API-DMAC7.html) |
| PL (1) | PL92913B1 (cg-RX-API-DMAC7.html) |
| SU (2) | SU643084A3 (cg-RX-API-DMAC7.html) |
-
1971
- 1971-12-21 NO NO475371A patent/NO133229C/no unknown
- 1971-12-23 IL IL38439A patent/IL38439A/en unknown
- 1971-12-30 IE IE165071A patent/IE35926B1/xx unknown
-
1972
- 1972-01-04 FI FI1072A patent/FI53315C/fi active
- 1972-01-07 CS CS681774A patent/CS166798B2/cs unknown
- 1972-01-07 ES ES398670A patent/ES398670A1/es not_active Expired
- 1972-01-07 HU HUCI001200 patent/HU166687B/hu unknown
- 1972-01-07 CS CS681672A patent/CS166797B2/cs unknown
- 1972-01-07 CS CS10872A patent/CS166796B2/cs unknown
- 1972-01-07 AR AR23997572A patent/AR192608A1/es active
- 1972-01-08 PL PL15281872A patent/PL92913B1/pl unknown
- 1972-11-02 AR AR24493872A patent/AR192674A1/es active
- 1972-11-02 AR AR24493772A patent/AR192673A1/es active
-
1973
- 1973-07-10 SU SU731945861A patent/SU643084A3/ru active
- 1973-07-10 SU SU1945862A patent/SU520046A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS166796B2 (cg-RX-API-DMAC7.html) | 1976-03-29 |
| IL38439A (en) | 1974-12-31 |
| NO133229B (cg-RX-API-DMAC7.html) | 1975-12-22 |
| AR192673A1 (es) | 1973-02-28 |
| SU442597A3 (ru) | 1974-09-05 |
| SU520046A3 (ru) | 1976-06-30 |
| CS166798B2 (cg-RX-API-DMAC7.html) | 1976-03-29 |
| CS166797B2 (cg-RX-API-DMAC7.html) | 1976-03-29 |
| FI53315B (cg-RX-API-DMAC7.html) | 1977-12-30 |
| ES398670A1 (es) | 1975-05-16 |
| FI53315C (fi) | 1978-04-10 |
| IE35926B1 (en) | 1976-06-23 |
| AR192608A1 (es) | 1973-02-28 |
| IE35926L (en) | 1972-07-08 |
| HU166687B (cg-RX-API-DMAC7.html) | 1975-05-28 |
| IL38439A0 (en) | 1972-02-29 |
| AR192674A1 (es) | 1973-02-28 |
| PL92913B1 (cg-RX-API-DMAC7.html) | 1977-04-30 |
| NO133229C (cg-RX-API-DMAC7.html) | 1976-03-31 |
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