BE634208A - - Google Patents
Info
- Publication number
- BE634208A BE634208A BE634208DA BE634208A BE 634208 A BE634208 A BE 634208A BE 634208D A BE634208D A BE 634208DA BE 634208 A BE634208 A BE 634208A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- formula
- compound
- methylamino
- ketone
- Prior art date
Links
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 claims 1
- SPUSRSAJDLMFHW-UHFFFAOYSA-N 2-ethyl-2-(methylamino)-1-phenylbutan-1-one Chemical compound CCC(CC)(NC)C(=O)C1=CC=CC=C1 SPUSRSAJDLMFHW-UHFFFAOYSA-N 0.000 claims 1
- PVHNKILPLXXDDZ-UHFFFAOYSA-N 2-phenylcycloheptan-1-one Chemical compound O=C1CCCCCC1C1=CC=CC=C1 PVHNKILPLXXDDZ-UHFFFAOYSA-N 0.000 claims 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- -1 2-methylamino-2-thiophenylcyclohexanone Chemical compound 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- ZAGBSZSITDFFAF-UHFFFAOYSA-N 2-(methylamino)-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(NC)CCCCC1=O ZAGBSZSITDFFAF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- FLMZBCWNWQCQDL-UHFFFAOYSA-N bis[2-[1-(ethylamino)cyclopentyl]-4-methylphenyl]methanone Chemical compound C(C)NC1(CCCC1)C1=C(C=CC(=C1)C)C(=O)C1=C(C=C(C=C1)C)C1(CCCC1)NCC FLMZBCWNWQCQDL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VWEZFLADPWFUNE-UHFFFAOYSA-N 1-[2-chloro-3-[C-[2-chloro-3-(1-hydroxycyclopentyl)phenyl]-N-methylcarbonimidoyl]phenyl]cyclopentan-1-ol Chemical compound CN=C(C1=C(C(=CC=C1)C1(CCCC1)O)Cl)C1=C(C(=CC=C1)C1(CCCC1)O)Cl VWEZFLADPWFUNE-UHFFFAOYSA-N 0.000 description 1
- LKENTYLPIUIMFG-UHFFFAOYSA-N 1-cyclopentylethanone Chemical compound CC(=O)C1CCCC1 LKENTYLPIUIMFG-UHFFFAOYSA-N 0.000 description 1
- NDVCZDFFOQKAGV-UHFFFAOYSA-N 2-(3-chlorophenyl)-2-(methylamino)cyclohexan-1-one Chemical compound C=1C=CC(Cl)=CC=1C1(NC)CCCCC1=O NDVCZDFFOQKAGV-UHFFFAOYSA-N 0.000 description 1
- PNEBONINASZRES-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-(methylamino)cyclohexan-1-one Chemical compound CNC1(C(CCCC1)=O)C1=CC(=CC=C1)O PNEBONINASZRES-UHFFFAOYSA-N 0.000 description 1
- FDIWKCNDYVHZLC-UHFFFAOYSA-N 2-(4-methylphenyl)-2-(pentylamino)cyclohexan-1-one Chemical compound C(CCCC)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C FDIWKCNDYVHZLC-UHFFFAOYSA-N 0.000 description 1
- GEHJFMOOKBKKLG-UHFFFAOYSA-N 2-(butylamino)-2-phenylcyclohexan-1-one Chemical compound C(CCC)NC1(C(CCCC1)=O)C1=CC=CC=C1 GEHJFMOOKBKKLG-UHFFFAOYSA-N 0.000 description 1
- IDLSBAANXISGEI-UHFFFAOYSA-N 2-(ethylamino)-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1=O IDLSBAANXISGEI-UHFFFAOYSA-N 0.000 description 1
- DFZAIVLIQFZJJL-UHFFFAOYSA-N 2-(methylamino)-2-(2-methylphenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(C)C=1C1(NC)CCCCC1=O DFZAIVLIQFZJJL-UHFFFAOYSA-N 0.000 description 1
- UKSNXZFQBYOUHW-UHFFFAOYSA-N 2-(methylamino)-2-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound CNC1(C(CCCC1)=O)C1=CC(=CC=C1)OCC1=CC=CC=C1 UKSNXZFQBYOUHW-UHFFFAOYSA-N 0.000 description 1
- LMYKPGOMBOFCPO-UHFFFAOYSA-N 2-(methylamino)-2-phenylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1C1(NC)CCCCC1O LMYKPGOMBOFCPO-UHFFFAOYSA-N 0.000 description 1
- KJMDOBYGKOIRQI-UHFFFAOYSA-N 2-(methylamino)-2-phenylcyclohexan-1-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(NC)CCCCC1=O KJMDOBYGKOIRQI-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
- QCXKLSJCXITLHD-UHFFFAOYSA-N 2-methyl-2-(methylamino)-1-phenylbutan-1-one Chemical compound CCC(C)(NC)C(=O)C1=CC=CC=C1 QCXKLSJCXITLHD-UHFFFAOYSA-N 0.000 description 1
- JLVGGPQTLAPRPH-UHFFFAOYSA-N 2-methyl-2-(methylamino)-1-phenylpropan-1-one Chemical compound CNC(C)(C)C(=O)C1=CC=CC=C1 JLVGGPQTLAPRPH-UHFFFAOYSA-N 0.000 description 1
- WNABJQWOGGCFLO-UHFFFAOYSA-N 2-phenyl-2-(propan-2-ylamino)cyclohexan-1-one Chemical compound CC(C)NC1(CCCCC1=O)C1=CC=CC=C1 WNABJQWOGGCFLO-UHFFFAOYSA-N 0.000 description 1
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 1
- RKPGYMUBNMEVJS-UHFFFAOYSA-N 3-(methylamino)-3-phenylbutan-2-one Chemical compound CNC(C)(C(C)=O)C1=CC=CC=C1 RKPGYMUBNMEVJS-UHFFFAOYSA-N 0.000 description 1
- KAYAIBFWOUTDTB-UHFFFAOYSA-N 3-(methylamino)-3-phenylbutan-2-one;hydrochloride Chemical compound Cl.CNC(C)(C(C)=O)C1=CC=CC=C1 KAYAIBFWOUTDTB-UHFFFAOYSA-N 0.000 description 1
- YSQNWYVHBOXDIY-UHFFFAOYSA-N 4-(methylamino)-4-phenylhexan-3-one Chemical compound CCC(=O)C(CC)(NC)C1=CC=CC=C1 YSQNWYVHBOXDIY-UHFFFAOYSA-N 0.000 description 1
- RLJVSZAGIWSNRH-UHFFFAOYSA-N BrC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)Br Chemical compound BrC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)Br RLJVSZAGIWSNRH-UHFFFAOYSA-N 0.000 description 1
- IPOXCLSOIFPFNR-UHFFFAOYSA-N BrC1(CCCC1)C1=C(C=CC=C1OC)C(=O)C1=C(C(=CC=C1)OC)C1(CCCC1)Br Chemical compound BrC1(CCCC1)C1=C(C=CC=C1OC)C(=O)C1=C(C(=CC=C1)OC)C1(CCCC1)Br IPOXCLSOIFPFNR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IDFPTMMFVSRILW-UHFFFAOYSA-N C(C)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C Chemical compound C(C)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C IDFPTMMFVSRILW-UHFFFAOYSA-N 0.000 description 1
- BLGXOZLPVNNOHH-UHFFFAOYSA-N CNC1(CCCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCCC1)NC Chemical compound CNC1(CCCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCCC1)NC BLGXOZLPVNNOHH-UHFFFAOYSA-N 0.000 description 1
- ODXHNAGNKODNQS-UHFFFAOYSA-N COC1(OC12CCCC2)C2=CC=CC=C2 Chemical compound COC1(OC12CCCC2)C2=CC=CC=C2 ODXHNAGNKODNQS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000002740 Muscle Rigidity Diseases 0.000 description 1
- FGMHITLDGGNXED-UHFFFAOYSA-N OC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)O Chemical compound OC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)O FGMHITLDGGNXED-UHFFFAOYSA-N 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- KTDJZBFLBCWTLC-UHFFFAOYSA-N acetic acid 2-(methylamino)-2-phenylcyclohexan-1-one Chemical group C(C)(=O)O.CNC1(C(CCCC1)=O)C1=CC=CC=C1 KTDJZBFLBCWTLC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AMEDKBHURXXSQO-UHFFFAOYSA-N azonous acid Chemical class ONO AMEDKBHURXXSQO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- ULFXZLBNZZIHJH-UHFFFAOYSA-N bis[1-(3-methoxyphenyl)cyclopentyl]methanone Chemical compound COC=1C=C(C=CC1)C1(CCCC1)C(=O)C1(CCCC1)C1=CC(=CC=C1)OC ULFXZLBNZZIHJH-UHFFFAOYSA-N 0.000 description 1
- ZOAQLIJZJVAOLU-UHFFFAOYSA-N bis[1-(4-methoxyphenyl)cyclopentyl]methanone Chemical compound COC1=CC=C(C=C1)C1(CCCC1)C(=O)C1(CCCC1)C1=CC=C(C=C1)OC ZOAQLIJZJVAOLU-UHFFFAOYSA-N 0.000 description 1
- AWKQNQLDOHLGQD-UHFFFAOYSA-N bis[3-(1-bromocyclopentyl)-2-methylphenyl]methanone Chemical compound BrC1(CCCC1)C=1C(=C(C=CC1)C(=O)C1=C(C(=CC=C1)C1(CCCC1)Br)C)C AWKQNQLDOHLGQD-UHFFFAOYSA-N 0.000 description 1
- PDZWNMQZHHUYFI-UHFFFAOYSA-N bis[3-methyl-2-[1-(propan-2-ylamino)cyclopentyl]phenyl]methanone Chemical compound C(C)(C)NC1(CCCC1)C1=C(C=CC=C1C)C(=O)C1=C(C(=CC=C1)C)C1(CCCC1)NC(C)C PDZWNMQZHHUYFI-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- ATPGKQPKLIKHTF-UHFFFAOYSA-N cyclopentyl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1CCCC1 ATPGKQPKLIKHTF-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- ISWNAMNOYHCTSB-UHFFFAOYSA-N methanamine;hydrobromide Chemical compound [Br-].[NH3+]C ISWNAMNOYHCTSB-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000021542 voluntary musculoskeletal movement Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR939698A FR1367034A (fr) | 1963-06-28 | 1963-06-28 | Procédé de production d'aminocétones |
Publications (1)
Publication Number | Publication Date |
---|---|
BE634208A true BE634208A (en, 2012) |
Family
ID=8807154
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE634208D BE634208A (en, 2012) | 1963-06-28 |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE634208A (en, 2012) |
FR (1) | FR1367034A (en, 2012) |
NL (1) | NL294634A (en, 2012) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1300953B (de) * | 1965-03-19 | 1969-08-14 | Parke Davis & Co | 2-(AEthylamino)-2-(2-thienyl)-cyclohexanon, dessen Additionssalze und Verfahren zu deren Herstellung |
-
0
- BE BE634208D patent/BE634208A/fr unknown
- NL NL294634D patent/NL294634A/xx unknown
-
1963
- 1963-06-28 FR FR939698A patent/FR1367034A/fr not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1300953B (de) * | 1965-03-19 | 1969-08-14 | Parke Davis & Co | 2-(AEthylamino)-2-(2-thienyl)-cyclohexanon, dessen Additionssalze und Verfahren zu deren Herstellung |
Also Published As
Publication number | Publication date |
---|---|
FR1367034A (fr) | 1964-07-17 |
NL294634A (en, 2012) |
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