LT3038B - Heterobicyclic compounds - Google Patents

Info

Publication number

LT3038B

LT3038B LTIP354A LTIP354A LT3038B LT 3038 B LT3038 B LT 3038B LT IP354 A LTIP354 A LT IP354A LT IP354 A LTIP354 A LT IP354A LT 3038 B LT3038 B LT 3038B

Authority

LT

Lithuania

Prior art keywords

methyl

oxo

benzopyran

phenyl

piperazinyl

Prior art date

1992-02-25

Links

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• 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 455
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 10
• 239000000651 prodrug Substances 0.000 claims abstract description 9
• 229940002612 prodrug Drugs 0.000 claims abstract description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims abstract 3
• -1 hydroxymethylene group Chemical group 0.000 claims description 228
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 169
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 64
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 46
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 41
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• LPACBRAWRCXZGB-UHFFFAOYSA-N 3-methyl-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LPACBRAWRCXZGB-UHFFFAOYSA-N 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical compound O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000006308 propyl amino group Chemical group 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
• JCIDEANDDNSHQC-UHFFFAOYSA-N 4H-chromene Chemical compound C1=CC=C2CC=COC2=C1 JCIDEANDDNSHQC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004442 acylamino group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
• 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 4
• OJXOWGJHAMWLIZ-UHFFFAOYSA-N 2-phenyl-4h-chromene Chemical compound O1C2=CC=CC=C2CC=C1C1=CC=CC=C1 OJXOWGJHAMWLIZ-UHFFFAOYSA-N 0.000 claims description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• IJNREAGEYUEUGU-UHFFFAOYSA-N 6-bromo-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(Br)C=2)CC1 IJNREAGEYUEUGU-UHFFFAOYSA-N 0.000 claims description 2
• GEHDMIHNCABTQT-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfanyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCSC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 GEHDMIHNCABTQT-UHFFFAOYSA-N 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000005277 alkyl imino group Chemical group 0.000 claims description 2
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000003435 aroyl group Chemical group 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 2
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• 125000004193 piperazinyl group Chemical group 0.000 claims 2
• AIHBTWJKGJLMQK-UHFFFAOYSA-N 1-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-(3-methyl-4-oxo-2-phenylchromen-8-yl)urea Chemical compound COC1=CC=CC=C1N1CCN(CCNC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 AIHBTWJKGJLMQK-UHFFFAOYSA-N 0.000 claims 1
• NCIOCKHTDZICDA-UHFFFAOYSA-N 3-(hydroxymethyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(CO)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 NCIOCKHTDZICDA-UHFFFAOYSA-N 0.000 claims 1
• AMUIEDQXJUZYCZ-UHFFFAOYSA-N 3-methyl-8-[2-[4-(2-methylphenyl)piperazin-1-yl]acetyl]-2-phenylchromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 AMUIEDQXJUZYCZ-UHFFFAOYSA-N 0.000 claims 1
• SOSSYEZSNHOGLE-UHFFFAOYSA-N 3-methyl-n-[3-[methyl-(1-oxo-3,4-dihydro-2h-naphthalen-2-yl)amino]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1CC2=CC=CC=C2C(=O)C1N(C)CCCNC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 SOSSYEZSNHOGLE-UHFFFAOYSA-N 0.000 claims 1
• JDAUINVSCGMHMP-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)butanamide Chemical compound COC1=CC=CC=C1N1CCN(CCCC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 JDAUINVSCGMHMP-UHFFFAOYSA-N 0.000 claims 1
• NUXJIGIXAYKHLS-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 NUXJIGIXAYKHLS-UHFFFAOYSA-N 0.000 claims 1
• DIINRQCXLCEVHL-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 DIINRQCXLCEVHL-UHFFFAOYSA-N 0.000 claims 1
• CVIYJJLZWPEVRU-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propanoyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 CVIYJJLZWPEVRU-UHFFFAOYSA-N 0.000 claims 1
• FMYFHINQACBOCS-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 FMYFHINQACBOCS-UHFFFAOYSA-N 0.000 claims 1
• ATFLWMRUEKKWBC-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 ATFLWMRUEKKWBC-UHFFFAOYSA-N 0.000 claims 1
• TTWAZPUHJYFZBE-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfonyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCS(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 TTWAZPUHJYFZBE-UHFFFAOYSA-N 0.000 claims 1
• WBWMQLSFKCZZKH-UHFFFAOYSA-N 8-[[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl-methylamino]methyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCN(C)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 WBWMQLSFKCZZKH-UHFFFAOYSA-N 0.000 claims 1
• AJLQOIWTUULSNB-UHFFFAOYSA-N [8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylcarbamoyl]-3-methyl-4-oxo-2-phenylchromen-6-yl] acetate Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(OC(C)=O)C=2)CC1 AJLQOIWTUULSNB-UHFFFAOYSA-N 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
• 239000004615 ingredient Substances 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• BUGZODXDBBCPKQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-(4-phenylphenyl)chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BUGZODXDBBCPKQ-UHFFFAOYSA-N 0.000 claims 1
• KXLPEPDVRPPMRV-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-pyridin-3-ylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=NC=CC=3)=O)C=CC=2)CC1 KXLPEPDVRPPMRV-UHFFFAOYSA-N 0.000 claims 1
• NPJCJQQKGMFUDQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C=CO3)=O)C=CC=2)CC1 NPJCJQQKGMFUDQ-UHFFFAOYSA-N 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 11
• 150000001412 amines Chemical class 0.000 abstract description 5
• 210000001635 urinary tract Anatomy 0.000 abstract description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 2
• 206010020772 Hypertension Diseases 0.000 abstract description 2
• 125000002947 alkylene group Chemical group 0.000 abstract description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
• 125000005842 heteroatom Chemical group 0.000 abstract description 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 1
• 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
• 201000010099 disease Diseases 0.000 abstract 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
• 125000005647 linker group Chemical group 0.000 abstract 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 466
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 358
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 333
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 332
• 239000000543 intermediate Substances 0.000 description 285
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 246
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 210
• 239000000243 solution Substances 0.000 description 206
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 198
• 239000000203 mixture Substances 0.000 description 166
• 239000002904 solvent Substances 0.000 description 163
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 142
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 125
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 116
• 238000006243 chemical reaction Methods 0.000 description 113
• 235000019439 ethyl acetate Nutrition 0.000 description 111
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 108
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
• 239000011541 reaction mixture Substances 0.000 description 84
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 83
• 239000002244 precipitate Substances 0.000 description 81
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
• 239000002585 base Substances 0.000 description 65
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 62
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 62
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
• 238000010992 reflux Methods 0.000 description 54
• 239000000741 silica gel Substances 0.000 description 52
• 229910002027 silica gel Inorganic materials 0.000 description 52
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
• 238000004587 chromatography analysis Methods 0.000 description 41
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
• 230000008018 melting Effects 0.000 description 39
• 238000002844 melting Methods 0.000 description 39
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 38
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 38
• 239000012044 organic layer Substances 0.000 description 38
• 238000000034 method Methods 0.000 description 36
• VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 35
• 230000002378 acidificating effect Effects 0.000 description 35
• 239000003208 petroleum Substances 0.000 description 35
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 34
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
• 238000003756 stirring Methods 0.000 description 32
• 229910000027 potassium carbonate Inorganic materials 0.000 description 31
• 229960000583 acetic acid Drugs 0.000 description 29
• 239000002253 acid Substances 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• 238000001914 filtration Methods 0.000 description 26
• 238000000746 purification Methods 0.000 description 26
• 238000010898 silica gel chromatography Methods 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000012074 organic phase Substances 0.000 description 24
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 23
• 239000012043 crude product Substances 0.000 description 23
• 239000007787 solid Substances 0.000 description 23
• 238000009835 boiling Methods 0.000 description 21
• 239000003054 catalyst Substances 0.000 description 21
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
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