CH650772A5 - Verfahren zur herstellung von pyrrolidin-2-onen aus 3-pyrrolin-2-onen und verfahren zur herstellung der 3-pyrrolin-2-on-ausgangsstoffe. - Google Patents
Verfahren zur herstellung von pyrrolidin-2-onen aus 3-pyrrolin-2-onen und verfahren zur herstellung der 3-pyrrolin-2-on-ausgangsstoffe. Download PDFInfo
- Publication number
- CH650772A5 CH650772A5 CH5496/79A CH549679A CH650772A5 CH 650772 A5 CH650772 A5 CH 650772A5 CH 5496/79 A CH5496/79 A CH 5496/79A CH 549679 A CH549679 A CH 549679A CH 650772 A5 CH650772 A5 CH 650772A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- formula
- aryl
- substituted
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- CDCHBOQVXIGZHA-UHFFFAOYSA-N 1,2-dihydropyrrol-5-one Chemical compound O=C1NCC=C1 CDCHBOQVXIGZHA-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003235 pyrrolidines Chemical class 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical class NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- -1 aromatic radicals Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KCUJZQHVIDHUQU-UHFFFAOYSA-N 3,4-diphenylpyrrolidine Chemical compound C1NCC(C=2C=CC=CC=2)C1C1=CC=CC=C1 KCUJZQHVIDHUQU-UHFFFAOYSA-N 0.000 description 3
- VNGGQUXNILKHIE-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC(=O)NC1 VNGGQUXNILKHIE-UHFFFAOYSA-N 0.000 description 3
- XWWQNFOFKPPMHY-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,5-dimethylpyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=C(Cl)C=C1 XWWQNFOFKPPMHY-UHFFFAOYSA-N 0.000 description 3
- PDTLMKLERGEENQ-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CC(=O)NC1 PDTLMKLERGEENQ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- APBKZMJARWKEJO-UHFFFAOYSA-N 2-amino-1-[4-(trifluoromethyl)phenyl]ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(C(F)(F)F)C=C1 APBKZMJARWKEJO-UHFFFAOYSA-N 0.000 description 2
- GNWOFDWOUZXQPD-UHFFFAOYSA-N 3,4-diphenyl-1,2-dihydropyrrol-5-one Chemical compound O=C1NCC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GNWOFDWOUZXQPD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- JWUYOFJPYSNYFC-UHFFFAOYSA-N 1,2-dimethyl-3,4-diphenyl-2h-pyrrol-5-one Chemical compound CC1N(C)C(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JWUYOFJPYSNYFC-UHFFFAOYSA-N 0.000 description 1
- QLCPYHKRCGVOOA-UHFFFAOYSA-N 1,2-dimethyl-3-phenyl-2h-pyrrol-5-one Chemical compound CC1N(C)C(=O)C=C1C1=CC=CC=C1 QLCPYHKRCGVOOA-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HOEWCGCSKILLPY-UHFFFAOYSA-N 1,5-dimethyl-4-(4-nitrophenyl)pyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=C([N+]([O-])=O)C=C1 HOEWCGCSKILLPY-UHFFFAOYSA-N 0.000 description 1
- QCZVVNIEASUBIS-UHFFFAOYSA-N 1,5-dimethyl-4-phenylpyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=CC=C1 QCZVVNIEASUBIS-UHFFFAOYSA-N 0.000 description 1
- XMMJINSTYOLCCA-UHFFFAOYSA-N 1-benzyl-3-[4-(trifluoromethyl)phenyl]-2h-pyrrol-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C1)=CC(=O)N1CC1=CC=CC=C1 XMMJINSTYOLCCA-UHFFFAOYSA-N 0.000 description 1
- DHMVUKFVGBQDDA-UHFFFAOYSA-N 1-methyl-3-(4-methylphenyl)-4-phenyl-2h-pyrrol-5-one Chemical compound O=C1N(C)CC(C=2C=CC(C)=CC=2)=C1C1=CC=CC=C1 DHMVUKFVGBQDDA-UHFFFAOYSA-N 0.000 description 1
- QPBIBMGRFHVCJI-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)-3-phenylpyrrolidin-2-one Chemical compound O=C1N(C)CC(C=2C=CC(C)=CC=2)C1C1=CC=CC=C1 QPBIBMGRFHVCJI-UHFFFAOYSA-N 0.000 description 1
- SWLVHCWYTKNOAB-UHFFFAOYSA-N 2-(5-oxo-3-phenyl-1,2-dihydropyrrol-4-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=C(C=2C=CC=CC=2)CNC1=O SWLVHCWYTKNOAB-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- PMGYCIGYLNWVCH-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 PMGYCIGYLNWVCH-UHFFFAOYSA-N 0.000 description 1
- KEMCZWYPWCUGPE-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 KEMCZWYPWCUGPE-UHFFFAOYSA-N 0.000 description 1
- XZWCDKTUYKCMMH-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(=O)NCC1C1=CC=C(C(F)(F)F)C=C1 XZWCDKTUYKCMMH-UHFFFAOYSA-N 0.000 description 1
- SYUHPEZHTMIRMJ-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-phenylpyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(=O)NCC1C1=CC=CC=C1 SYUHPEZHTMIRMJ-UHFFFAOYSA-N 0.000 description 1
- LXZAVFHIIYGLTF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 LXZAVFHIIYGLTF-UHFFFAOYSA-N 0.000 description 1
- XRCJTMJEQCHAOB-UHFFFAOYSA-N 3-(4-methylphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 XRCJTMJEQCHAOB-UHFFFAOYSA-N 0.000 description 1
- QPGLUEKHBNOAHG-UHFFFAOYSA-N 3-carboxypropylazanium;chloride Chemical class Cl.NCCCC(O)=O QPGLUEKHBNOAHG-UHFFFAOYSA-N 0.000 description 1
- CVOQOLZRCXIRRT-UHFFFAOYSA-N 3-methyl-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1NC(=O)C(C)C1C1=CC=C(C(F)(F)F)C=C1 CVOQOLZRCXIRRT-UHFFFAOYSA-N 0.000 description 1
- USRGHTBNRODIGQ-UHFFFAOYSA-N 3-phenyl-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 USRGHTBNRODIGQ-UHFFFAOYSA-N 0.000 description 1
- JPMRXLUPEVYCNZ-UHFFFAOYSA-N 4-(2-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound FC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CNC1=O JPMRXLUPEVYCNZ-UHFFFAOYSA-N 0.000 description 1
- LIOVPXGQAPGNNY-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)CNC1=O LIOVPXGQAPGNNY-UHFFFAOYSA-N 0.000 description 1
- SDVNHWAFTHMIQR-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-phenylpyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 SDVNHWAFTHMIQR-UHFFFAOYSA-N 0.000 description 1
- PRNHHUOUMAWRJT-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-phenylpyrrolidin-2-one Chemical compound C1=CC(OC)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 PRNHHUOUMAWRJT-UHFFFAOYSA-N 0.000 description 1
- SSNGRNRNPOYPGF-UHFFFAOYSA-N 4-(4-methylphenyl)-3-phenylpyrrolidin-2-one Chemical compound C1=CC(C)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 SSNGRNRNPOYPGF-UHFFFAOYSA-N 0.000 description 1
- MUJPZGGZLAHFFQ-UHFFFAOYSA-N 4-(methylamino)-3-phenylpentanoic acid hydrochloride Chemical compound Cl.CNC(C)C(CC(O)=O)C1=CC=CC=C1 MUJPZGGZLAHFFQ-UHFFFAOYSA-N 0.000 description 1
- DSNFSXPDCZIZCB-UHFFFAOYSA-N 4-amino-2,3-diphenylbutanoic acid Chemical compound C=1C=CC=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1 DSNFSXPDCZIZCB-UHFFFAOYSA-N 0.000 description 1
- SLELWOSWONKPDI-UHFFFAOYSA-N 4-amino-2-(2-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1F SLELWOSWONKPDI-UHFFFAOYSA-N 0.000 description 1
- AXKPDYZORRWBOD-UHFFFAOYSA-N 4-amino-2-(4-fluorophenyl)-3-phenylbutanoic acid hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CN)C(C(O)=O)C1=CC=C(F)C=C1 AXKPDYZORRWBOD-UHFFFAOYSA-N 0.000 description 1
- MDJNQOXQCIGQTJ-UHFFFAOYSA-N 4-amino-2-phenyl-3-[4-(trifluoromethyl)phenyl]butanoic acid;hydrochloride Chemical compound Cl.C=1C=C(C(F)(F)F)C=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1 MDJNQOXQCIGQTJ-UHFFFAOYSA-N 0.000 description 1
- GAVYIBFSKZVARR-UHFFFAOYSA-N 4-amino-3-(4-fluorophenyl)-2-phenylbutanoic acid hydrochloride Chemical compound Cl.C=1C=C(F)C=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1 GAVYIBFSKZVARR-UHFFFAOYSA-N 0.000 description 1
- VFGHAQNYKTWWOM-UHFFFAOYSA-N 4-amino-3-(4-methylphenyl)-2-phenylbutanoic acid Chemical compound C1=CC(C)=CC=C1C(CN)C(C(O)=O)C1=CC=CC=C1 VFGHAQNYKTWWOM-UHFFFAOYSA-N 0.000 description 1
- FTSJDURWVUMKDO-UHFFFAOYSA-N 4-amino-3-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CC(CN)C1=CC=C(C(F)(F)F)C=C1 FTSJDURWVUMKDO-UHFFFAOYSA-N 0.000 description 1
- CHVOVFFXIYWDTJ-UHFFFAOYSA-N 4-amino-3-[4-(trifluoromethyl)phenyl]butanoic acid hydrochloride Chemical compound Cl.OC(=O)CC(CN)C1=CC=C(C(F)(F)F)C=C1 CHVOVFFXIYWDTJ-UHFFFAOYSA-N 0.000 description 1
- DQOSOTIKDZAXKT-UHFFFAOYSA-N 4-phenyl-3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 DQOSOTIKDZAXKT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JHRDATNCTTVZBE-UHFFFAOYSA-N Cl.OC(=O)C(C)C(CN)C1=CC=C(C(F)(F)F)C=C1 Chemical compound Cl.OC(=O)C(C)C(CN)C1=CC=C(C(F)(F)F)C=C1 JHRDATNCTTVZBE-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DJEBTLRMBZNIIF-UHFFFAOYSA-N n-phenacyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)CC1=CC=CC=C1 DJEBTLRMBZNIIF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91468278A | 1978-06-12 | 1978-06-12 | |
| US1249679A | 1979-02-15 | 1979-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650772A5 true CH650772A5 (de) | 1985-08-15 |
Family
ID=26683628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5496/79A CH650772A5 (de) | 1978-06-12 | 1979-06-12 | Verfahren zur herstellung von pyrrolidin-2-onen aus 3-pyrrolin-2-onen und verfahren zur herstellung der 3-pyrrolin-2-on-ausgangsstoffe. |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR222997A1 (fi) |
| AT (1) | ATA386679A (fi) |
| AU (1) | AU529479B2 (fi) |
| CA (1) | CA1108628A (fi) |
| CH (1) | CH650772A5 (fi) |
| DE (3) | DE2954236C2 (fi) |
| DK (1) | DK157847C (fi) |
| ES (1) | ES481315A1 (fi) |
| FI (1) | FI70209C (fi) |
| FR (1) | FR2434151A1 (fi) |
| GB (1) | GB2028307B (fi) |
| GR (1) | GR68438B (fi) |
| IL (1) | IL57266A (fi) |
| IT (1) | IT1116891B (fi) |
| NL (1) | NL7904584A (fi) |
| NO (1) | NO791943L (fi) |
| NZ (1) | NZ190705A (fi) |
| PT (1) | PT69716A (fi) |
| SE (1) | SE431644B (fi) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943640A (en) * | 1983-10-14 | 1990-07-24 | The Dow Chemical Company | Preparation of 5-(1-alkyl-carbonyloxy)alkylpyrrolidin-2-one |
| AU4809390A (en) * | 1988-12-27 | 1990-08-01 | Ici Americas Inc. | Process for the preparation of 3-carboalkoxypyrrolidones |
| US5021587A (en) * | 1990-01-24 | 1991-06-04 | Petrolite Corporation | Synthesis of N,3,4-trisubstituted-3-azoline-2-ones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272842A (en) * | 1965-06-25 | 1966-09-13 | Lilly Co Eli | Novel pyrrolinones |
| GB1350582A (en) | 1970-07-24 | 1974-04-18 | Ucb Sa | Cerivatives of 2-pyrrolidinone |
| DE2413935A1 (de) | 1974-03-20 | 1975-10-16 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone |
-
1979
- 1979-05-14 IL IL57266A patent/IL57266A/xx unknown
- 1979-05-15 GR GR59088A patent/GR68438B/el unknown
- 1979-05-17 AR AR276559A patent/AR222997A1/es active
- 1979-05-28 AT AT793866A patent/ATA386679A/de not_active Application Discontinuation
- 1979-06-01 AU AU47670/79A patent/AU529479B2/en not_active Ceased
- 1979-06-01 PT PT69716A patent/PT69716A/pt unknown
- 1979-06-06 ES ES481315A patent/ES481315A1/es not_active Expired
- 1979-06-08 CA CA329,322A patent/CA1108628A/en not_active Expired
- 1979-06-09 DE DE2954236A patent/DE2954236C2/de not_active Expired
- 1979-06-09 DE DE2954237A patent/DE2954237C2/de not_active Expired
- 1979-06-09 DE DE19792923553 patent/DE2923553A1/de active Granted
- 1979-06-11 NO NO791943A patent/NO791943L/no unknown
- 1979-06-11 GB GB7920275A patent/GB2028307B/en not_active Expired
- 1979-06-11 IT IT49373/79A patent/IT1116891B/it active
- 1979-06-11 SE SE7905079A patent/SE431644B/sv not_active IP Right Cessation
- 1979-06-11 FR FR7914907A patent/FR2434151A1/fr active Granted
- 1979-06-11 DK DK241779A patent/DK157847C/da not_active IP Right Cessation
- 1979-06-12 CH CH5496/79A patent/CH650772A5/de not_active IP Right Cessation
- 1979-06-12 NL NL7904584A patent/NL7904584A/xx not_active Application Discontinuation
- 1979-06-12 NZ NZ190705A patent/NZ190705A/xx unknown
- 1979-06-12 FI FI791866A patent/FI70209C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1108628A (en) | 1981-09-08 |
| NZ190705A (en) | 1981-10-19 |
| GR68438B (fi) | 1981-12-30 |
| IL57266A0 (en) | 1979-09-30 |
| ES481315A1 (es) | 1980-08-16 |
| AU4767079A (en) | 1979-12-20 |
| IT7949373A0 (it) | 1979-06-11 |
| DE2923553A1 (de) | 1979-12-20 |
| DK241779A (da) | 1979-12-13 |
| DE2954236C2 (fi) | 1988-10-06 |
| NO791943L (no) | 1979-12-13 |
| FR2434151A1 (fr) | 1980-03-21 |
| FI70209B (fi) | 1986-02-28 |
| SE431644B (sv) | 1984-02-20 |
| DE2923553C2 (fi) | 1988-06-01 |
| GB2028307B (en) | 1983-01-19 |
| DK157847C (da) | 1990-09-17 |
| SE7905079L (sv) | 1979-12-13 |
| AR222997A1 (es) | 1981-07-15 |
| ATA386679A (de) | 1983-12-15 |
| NL7904584A (nl) | 1979-12-14 |
| GB2028307A (en) | 1980-03-05 |
| FR2434151B3 (fi) | 1982-04-30 |
| FI70209C (fi) | 1986-09-15 |
| DE2954237C2 (fi) | 1989-09-21 |
| PT69716A (en) | 1979-07-01 |
| AU529479B2 (en) | 1983-06-09 |
| IT1116891B (it) | 1986-02-10 |
| IL57266A (en) | 1982-12-31 |
| FI791866A (fi) | 1979-12-13 |
| DK157847B (da) | 1990-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |