SE460605B - Foerfarande foer framstaellning av 4-amino-1,2-hydrokarbyl-pyrazolidiner - Google Patents
Foerfarande foer framstaellning av 4-amino-1,2-hydrokarbyl-pyrazolidinerInfo
- Publication number
- SE460605B SE460605B SE8104677A SE8104677A SE460605B SE 460605 B SE460605 B SE 460605B SE 8104677 A SE8104677 A SE 8104677A SE 8104677 A SE8104677 A SE 8104677A SE 460605 B SE460605 B SE 460605B
- Authority
- SE
- Sweden
- Prior art keywords
- pyrazolidine
- amino
- nitro
- hydrocarbyl
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 1,3-bis (disubstituted amino) -2-nitropropane Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- NMTDWUVFGOBBAX-UHFFFAOYSA-N 1,2-diethylhydrazine;hydron;dichloride Chemical group Cl.Cl.CCNNCC NMTDWUVFGOBBAX-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002429 hydrazines Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- YCBOYOYVDOUXLH-UHFFFAOYSA-N 1,2-Diethylhydrazine Chemical compound CCNNCC YCBOYOYVDOUXLH-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- JOQGJRQKCIJIDB-UHFFFAOYSA-N tin;hydrochloride Chemical compound Cl.[Sn] JOQGJRQKCIJIDB-UHFFFAOYSA-N 0.000 claims description 2
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 150000003218 pyrazolidines Chemical class 0.000 claims 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims 1
- 235000019345 sodium thiosulphate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- MDCVHUGPELSGPR-UHFFFAOYSA-N 1,2-diethyl-4-nitropyrazolidine Chemical compound CCN1CC([N+]([O-])=O)CN1CC MDCVHUGPELSGPR-UHFFFAOYSA-N 0.000 description 5
- NYKKXRCUKXDUAL-UHFFFAOYSA-N 1,2-bis[(4-methoxyphenyl)methyl]hydrazine Chemical compound C1=CC(OC)=CC=C1CNNCC1=CC=C(OC)C=C1 NYKKXRCUKXDUAL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HSZDKPZQCXWNRJ-UHFFFAOYSA-N 4-(3-morpholin-4-yl-2-nitropropyl)morpholine Chemical compound C1COCCN1CC([N+](=O)[O-])CN1CCOCC1 HSZDKPZQCXWNRJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QWUBSELDPMNACM-UHFFFAOYSA-N 1,2-dibenzyl-4-nitropyrazolidine Chemical compound C=1C=CC=CC=1CN1CC([N+](=O)[O-])CN1CC1=CC=CC=C1 QWUBSELDPMNACM-UHFFFAOYSA-N 0.000 description 2
- UWMQDNXPZQCGLR-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]pyrazolidine Chemical compound C1=CC(OC)=CC=C1CN1NCCC1 UWMQDNXPZQCGLR-UHFFFAOYSA-N 0.000 description 2
- SISIYJVUHSSKDF-UHFFFAOYSA-N 1-benzyl-2-ethyl-4-nitropyrazolidine Chemical compound CCN1CC([N+]([O-])=O)CN1CC1=CC=CC=C1 SISIYJVUHSSKDF-UHFFFAOYSA-N 0.000 description 2
- SQZCNTOOLCFFEK-UHFFFAOYSA-N 1-benzyl-2-methyl-4-nitropyrazolidine Chemical compound CN1CC([N+]([O-])=O)CN1CC1=CC=CC=C1 SQZCNTOOLCFFEK-UHFFFAOYSA-N 0.000 description 2
- VFBFKWKOTGWBRW-UHFFFAOYSA-N 1-cyclohexyl-2-ethyl-4-nitropyrazolidine Chemical compound CCN1CC([N+]([O-])=O)CN1C1CCCCC1 VFBFKWKOTGWBRW-UHFFFAOYSA-N 0.000 description 2
- DJIYDGUUQZXROA-UHFFFAOYSA-N 1-cyclohexyl-2-methyl-4-nitropyrazolidine Chemical compound CN1CC([N+]([O-])=O)CN1C1CCCCC1 DJIYDGUUQZXROA-UHFFFAOYSA-N 0.000 description 2
- LZIXEBOQHPATHS-UHFFFAOYSA-N 1-ethyl-2-[(4-methoxyphenyl)methyl]-4-nitropyrazolidine Chemical compound CCN1CC([N+]([O-])=O)CN1CC1=CC=C(OC)C=C1 LZIXEBOQHPATHS-UHFFFAOYSA-N 0.000 description 2
- GBYVAMUMPLYRKT-UHFFFAOYSA-N 1-ethyl-2-methyl-4-nitropyrazolidine Chemical compound CCN1CC([N+]([O-])=O)CN1C GBYVAMUMPLYRKT-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000003960 organic solvent Substances 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 description 1
- NNQXUVSZVFKATP-UHFFFAOYSA-N 1,2-bis[(2,4-dimethoxyphenyl)methyl]hydrazine Chemical compound COC1=C(CNNCC2=C(C=C(C=C2)OC)OC)C=CC(=C1)OC NNQXUVSZVFKATP-UHFFFAOYSA-N 0.000 description 1
- GYHKJLONOKBXGG-UHFFFAOYSA-N 1,2-bis[(4-butoxyphenyl)methyl]hydrazine;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC(OCCCC)=CC=C1CNNCC1=CC=C(OCCCC)C=C1 GYHKJLONOKBXGG-UHFFFAOYSA-N 0.000 description 1
- GDEFXBGGXGAPIZ-UHFFFAOYSA-N 1,2-bis[(4-chlorophenyl)methyl]hydrazine;dihydrochloride Chemical compound Cl.Cl.C1=CC(Cl)=CC=C1CNNCC1=CC=C(Cl)C=C1 GDEFXBGGXGAPIZ-UHFFFAOYSA-N 0.000 description 1
- YQALJYOOPKKPRG-UHFFFAOYSA-N 1,2-bis[(4-methoxyphenyl)methyl]-4-nitropyrazolidine Chemical compound C1=CC(OC)=CC=C1CN1N(CC=2C=CC(OC)=CC=2)CC([N+]([O-])=O)C1 YQALJYOOPKKPRG-UHFFFAOYSA-N 0.000 description 1
- ZDZKKJSLYKHWRJ-UHFFFAOYSA-N 1,2-bis[[4-(trifluoromethyl)phenyl]methyl]hydrazine;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(F)(F)F)=CC=C1CNNCC1=CC=C(C(F)(F)F)C=C1 ZDZKKJSLYKHWRJ-UHFFFAOYSA-N 0.000 description 1
- HLBFSSOBHVYJQZ-UHFFFAOYSA-N 1,2-bis[[4-(trifluoromethyl)phenyl]methyl]pyrazolidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN1CC(N)CN1CC1=CC=C(C(F)(F)F)C=C1 HLBFSSOBHVYJQZ-UHFFFAOYSA-N 0.000 description 1
- ZAAZMYYPRQHZQS-UHFFFAOYSA-N 1,2-bis[butoxy(phenyl)methyl]pyrazolidin-4-amine Chemical compound C=1C=CC=CC=1C(OCCCC)N1CC(N)CN1C(OCCCC)C1=CC=CC=C1 ZAAZMYYPRQHZQS-UHFFFAOYSA-N 0.000 description 1
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- DYSSXVHZRFSJPX-UHFFFAOYSA-N 1,2-di(propan-2-yl)pyrazolidin-4-amine Chemical compound CC(C)N1CC(N)CN1C(C)C DYSSXVHZRFSJPX-UHFFFAOYSA-N 0.000 description 1
- GMPVTBNBIHAQBI-UHFFFAOYSA-N 1,2-dicyclohexylhydrazine;dihydrochloride Chemical compound Cl.Cl.C1CCCCC1NNC1CCCCC1 GMPVTBNBIHAQBI-UHFFFAOYSA-N 0.000 description 1
- IXNFVXVYMBENNM-UHFFFAOYSA-N 1,2-dicyclohexylpyrazolidin-4-amine Chemical compound C1CCCCC1N1CC(N)CN1C1CCCCC1 IXNFVXVYMBENNM-UHFFFAOYSA-N 0.000 description 1
- OWYGVZUBTJDDJQ-UHFFFAOYSA-N 1,2-diethyl-3-nitropyrazolidine Chemical compound [N+](=O)([O-])C1N(N(CC1)CC)CC OWYGVZUBTJDDJQ-UHFFFAOYSA-N 0.000 description 1
- KMVXDWYGRNSDPF-UHFFFAOYSA-N 1,2-diethylhydrazine hydrate dihydrochloride Chemical compound O.Cl.Cl.CCNNCC KMVXDWYGRNSDPF-UHFFFAOYSA-N 0.000 description 1
- GQKOXBZTNMLZQH-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2-ethylhydrazine;dihydrochloride Chemical compound Cl.Cl.CCNNCC1=CC=C(Cl)C=C1 GQKOXBZTNMLZQH-UHFFFAOYSA-N 0.000 description 1
- QPTLAGDMDPVELY-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2-ethylpyrazolidin-4-amine Chemical compound CCN1CC(N)CN1CC1=CC=C(Cl)C=C1 QPTLAGDMDPVELY-UHFFFAOYSA-N 0.000 description 1
- GPCXCRPRPVZMNV-UHFFFAOYSA-N 1-benzyl-2-ethylhydrazine;dihydrochloride Chemical compound Cl.Cl.CCNNCC1=CC=CC=C1 GPCXCRPRPVZMNV-UHFFFAOYSA-N 0.000 description 1
- QLQLOVCAKRWREX-UHFFFAOYSA-N 1-benzyl-2-ethylpyrazolidin-4-amine Chemical compound CCN1CC(N)CN1CC1=CC=CC=C1 QLQLOVCAKRWREX-UHFFFAOYSA-N 0.000 description 1
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- NNRDMDHLPHFDSE-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1CC1=CC=CC=C1 NNRDMDHLPHFDSE-UHFFFAOYSA-N 0.000 description 1
- PVFUJNXTCINPIS-UHFFFAOYSA-N 1-benzylpyrazolidine Chemical compound C=1C=CC=CC=1CN1CCCN1 PVFUJNXTCINPIS-UHFFFAOYSA-N 0.000 description 1
- IEICUBIEYICWTM-UHFFFAOYSA-N 1-cyclohexyl-2-ethylhydrazine;dihydrochloride Chemical compound Cl.Cl.CCNNC1CCCCC1 IEICUBIEYICWTM-UHFFFAOYSA-N 0.000 description 1
- YMCXGGKBIIBFEK-UHFFFAOYSA-N 1-cyclohexyl-2-ethylpyrazolidin-4-amine Chemical compound CCN1CC(N)CN1C1CCCCC1 YMCXGGKBIIBFEK-UHFFFAOYSA-N 0.000 description 1
- XYUOOPRAZMJZIY-UHFFFAOYSA-N 1-cyclohexyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1C1CCCCC1 XYUOOPRAZMJZIY-UHFFFAOYSA-N 0.000 description 1
- OUFDLHDFCWPFKY-UHFFFAOYSA-N 1-ethyl-2-[(4-methoxyphenyl)methyl]pyrazolidin-4-amine Chemical compound CCN1CC(N)CN1CC1=CC=C(OC)C=C1 OUFDLHDFCWPFKY-UHFFFAOYSA-N 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- TZNBFFOIJFSWGW-UHFFFAOYSA-N ethyl(ethylamino)azanium;chloride Chemical compound Cl.CCNNCC TZNBFFOIJFSWGW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- HHFHXLJKKDXLQT-UHFFFAOYSA-N n,n,n',n'-tetramethyl-2-nitropropane-1,3-diamine Chemical compound CN(C)CC([N+]([O-])=O)CN(C)C HHFHXLJKKDXLQT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BBDOMHXDXUDXPB-UHFFFAOYSA-N n-pyrazolidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CNNC1 BBDOMHXDXUDXPB-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/176,175 US4309552A (en) | 1980-08-07 | 1980-08-07 | Synthesis of 4-nitro-1,2-hydrocarbyl pyrazolidines and process for preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8104677L SE8104677L (sv) | 1982-02-08 |
| SE460605B true SE460605B (sv) | 1989-10-30 |
Family
ID=22643300
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8104677A SE460605B (sv) | 1980-08-07 | 1981-08-04 | Foerfarande foer framstaellning av 4-amino-1,2-hydrokarbyl-pyrazolidiner |
| SE8703254A SE8703254L (sv) | 1980-08-07 | 1987-08-21 | Syntes av 4-amino-1,2-hydrokarbyl-pyrazolidiner via 4-nitroanaloger |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8703254A SE8703254L (sv) | 1980-08-07 | 1987-08-21 | Syntes av 4-amino-1,2-hydrokarbyl-pyrazolidiner via 4-nitroanaloger |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4309552A (da) |
| JP (2) | JPS5759868A (da) |
| KR (1) | KR840001562B1 (da) |
| AT (1) | AT378184B (da) |
| AU (1) | AU539796B2 (da) |
| BE (1) | BE889878A (da) |
| CA (1) | CA1164001A (da) |
| CH (1) | CH652121A5 (da) |
| DE (1) | DE3130833A1 (da) |
| DK (1) | DK151625C (da) |
| EG (1) | EG16445A (da) |
| ES (2) | ES8502096A1 (da) |
| FI (1) | FI74952C (da) |
| FR (2) | FR2490639A1 (da) |
| GB (1) | GB2081713B (da) |
| HK (1) | HK485A (da) |
| HU (2) | HU191978B (da) |
| IE (1) | IE51530B1 (da) |
| IL (1) | IL63218A (da) |
| IT (1) | IT1144824B (da) |
| NL (1) | NL8103739A (da) |
| NO (1) | NO156009C (da) |
| NZ (1) | NZ197952A (da) |
| PH (2) | PH17183A (da) |
| PT (1) | PT73489B (da) |
| SE (2) | SE460605B (da) |
| SG (1) | SG62138G (da) |
| YU (2) | YU43498B (da) |
| ZA (1) | ZA814514B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3065506B2 (ja) | 1995-04-03 | 2000-07-17 | 株式会社資生堂 | ピラゾリジン誘導体及びラジカルスカベンジャー、脳梗塞抑制剤、脳浮腫抑制剤 |
| CA2469435A1 (en) * | 2001-12-21 | 2003-07-24 | X-Ceptor Therapeutics, Inc. | Modulators of lxr |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660426A (en) * | 1969-06-25 | 1972-05-02 | Robins Co Inc A H | Process for the preparation of 4-pyrazolidinols |
| PH13331A (en) * | 1977-08-19 | 1980-03-13 | Robins Co Inc A H | N-(4-pyrazolidinyl)-benzamides,composition and method of use thereof |
| US4207327A (en) * | 1977-08-19 | 1980-06-10 | A. H. Robins Company, Inc. | N-(4-Pyrazolidinyl)benzamides and their amino precursors |
-
1980
- 1980-08-07 US US06/176,175 patent/US4309552A/en not_active Expired - Lifetime
-
1981
- 1981-07-01 IL IL63218A patent/IL63218A/xx unknown
- 1981-07-02 ZA ZA814514A patent/ZA814514B/xx unknown
- 1981-07-22 EG EG420/81A patent/EG16445A/xx active
- 1981-07-27 YU YU1848/81A patent/YU43498B/xx unknown
- 1981-07-28 AT AT0333181A patent/AT378184B/de not_active IP Right Cessation
- 1981-07-29 IE IE1721/81A patent/IE51530B1/en unknown
- 1981-07-31 GB GB8123470A patent/GB2081713B/en not_active Expired
- 1981-07-31 SG SG263/84A patent/SG62138G/en unknown
- 1981-08-04 PH PH26001A patent/PH17183A/en unknown
- 1981-08-04 DE DE19813130833 patent/DE3130833A1/de not_active Ceased
- 1981-08-04 SE SE8104677A patent/SE460605B/sv not_active IP Right Cessation
- 1981-08-05 ES ES504558A patent/ES8502096A1/es not_active Expired
- 1981-08-05 CA CA000383277A patent/CA1164001A/en not_active Expired
- 1981-08-05 DK DK348781A patent/DK151625C/da not_active IP Right Cessation
- 1981-08-06 HU HU844475A patent/HU191978B/hu not_active IP Right Cessation
- 1981-08-06 PT PT73489A patent/PT73489B/pt unknown
- 1981-08-06 BE BE0/205598A patent/BE889878A/fr not_active IP Right Cessation
- 1981-08-06 KR KR1019810002859A patent/KR840001562B1/ko active
- 1981-08-06 IT IT68098/81A patent/IT1144824B/it active
- 1981-08-06 NO NO812671A patent/NO156009C/no unknown
- 1981-08-06 FR FR8115297A patent/FR2490639A1/fr active Granted
- 1981-08-06 HU HU812277A patent/HU187350B/hu not_active IP Right Cessation
- 1981-08-06 CH CH5074/81A patent/CH652121A5/fr not_active IP Right Cessation
- 1981-08-06 FI FI812433A patent/FI74952C/fi not_active IP Right Cessation
- 1981-08-06 NZ NZ197952A patent/NZ197952A/en unknown
- 1981-08-07 NL NL8103739A patent/NL8103739A/nl unknown
- 1981-08-07 JP JP56123973A patent/JPS5759868A/ja active Pending
- 1981-08-07 AU AU73875/81A patent/AU539796B2/en not_active Ceased
- 1981-11-06 FR FR8120878A patent/FR2491065A1/fr active Granted
-
1982
- 1982-07-27 ES ES514414A patent/ES8307752A1/es not_active Expired
-
1983
- 1983-08-29 YU YU01766/83A patent/YU176683A/xx unknown
- 1983-11-11 PH PH29863A patent/PH17530A/en unknown
-
1985
- 1985-01-03 HK HK4/85A patent/HK485A/xx unknown
-
1987
- 1987-08-21 SE SE8703254A patent/SE8703254L/xx not_active Application Discontinuation
-
1990
- 1990-11-30 JP JP2337025A patent/JPH03204859A/ja active Pending
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