BE613443A - - Google Patents
Info
- Publication number
- BE613443A BE613443A BE613443DA BE613443A BE 613443 A BE613443 A BE 613443A BE 613443D A BE613443D A BE 613443DA BE 613443 A BE613443 A BE 613443A
- Authority
- BE
- Belgium
- Prior art keywords
- hydroxybenzyl
- general formula
- solution
- acid
- nitrosamine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- -1 N- (3-hydroxybenzyl) -N-methylhydrazinium oxalate Chemical compound 0.000 claims description 61
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 239000011780 sodium chloride Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000007792 addition Methods 0.000 claims description 13
- 150000007857 hydrazones Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 230000000875 corresponding Effects 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
- 150000002429 hydrazines Chemical class 0.000 claims description 11
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- CIJBKNZDKBKMFU-UHFFFAOYSA-N N-nitrosomethanamine Chemical compound CNN=O CIJBKNZDKBKMFU-UHFFFAOYSA-N 0.000 claims description 7
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 238000001256 steam distillation Methods 0.000 claims description 6
- JVUOJMODQRWSRP-UHFFFAOYSA-N 3-(methylaminomethyl)phenol Chemical compound CNCC1=CC=CC(O)=C1 JVUOJMODQRWSRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 80
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 239000000047 product Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 28
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 238000001953 recrystallisation Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229960000583 Acetic Acid Drugs 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 7
- 210000001772 Blood Platelets Anatomy 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 235000006408 oxalic acid Nutrition 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000004429 atoms Chemical group 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- RXPWVQTZHIFHTC-UHFFFAOYSA-N 2-[[amino(methyl)amino]methyl]phenol Chemical compound CN(N)CC1=CC=CC=C1O RXPWVQTZHIFHTC-UHFFFAOYSA-N 0.000 description 3
- ZUMILRSHURBTSU-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC1=C(C[NH2+]C)C=CC=C1Br Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC1=C(C[NH2+]C)C=CC=C1Br ZUMILRSHURBTSU-UHFFFAOYSA-N 0.000 description 3
- GAOAYHKSPGHKBL-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]CC)C=CC=1 Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]CC)C=CC=1 GAOAYHKSPGHKBL-UHFFFAOYSA-N 0.000 description 3
- QJQBPNNXXCDONV-UHFFFAOYSA-N [Cl-].CC1=CC=C(C=C1)S(=O)(=O)OC1=C(C[NH2+]C)C=CC=C1 Chemical compound [Cl-].CC1=CC=C(C=C1)S(=O)(=O)OC1=C(C[NH2+]C)C=CC=C1 QJQBPNNXXCDONV-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000005712 crystallization Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N 8-Hydroxyquinoline Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- DQPCBMRVFMSMGJ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CBr)C=CC=1 Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CBr)C=CC=1 DQPCBMRVFMSMGJ-UHFFFAOYSA-N 0.000 description 2
- MMTBYLPLKIVZAW-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CN(N)C)C(=CC=1)Br Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CN(N)C)C(=CC=1)Br MMTBYLPLKIVZAW-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N Mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- CXMQXDZEQIYTIO-UHFFFAOYSA-O OC=1C=C(C[NH+](N)C)C(=CC=1)Br Chemical compound OC=1C=C(C[NH+](N)C)C(=CC=1)Br CXMQXDZEQIYTIO-UHFFFAOYSA-O 0.000 description 2
- BJJDPKGXTMVSKI-UHFFFAOYSA-O OC=1C=C(C[NH+](N)C)C=CC=1 Chemical compound OC=1C=C(C[NH+](N)C)C=CC=1 BJJDPKGXTMVSKI-UHFFFAOYSA-O 0.000 description 2
- HCDMVVJKWLYPOS-UHFFFAOYSA-O OC=1C=C(C[NH+](N)CC)C=CC=1 Chemical compound OC=1C=C(C[NH+](N)CC)C=CC=1 HCDMVVJKWLYPOS-UHFFFAOYSA-O 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- TWAPBBSHKKKTAB-UHFFFAOYSA-N [Cl-].BrC=1C=C(C[NH2+]C)C(=CC=1)O Chemical compound [Cl-].BrC=1C=C(C[NH2+]C)C(=CC=1)O TWAPBBSHKKKTAB-UHFFFAOYSA-N 0.000 description 2
- YVWPOPOAEBMXPE-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Br Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Br YVWPOPOAEBMXPE-UHFFFAOYSA-N 0.000 description 2
- BOBWOVWNFFQTDS-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]CC)C(=CC=1)Cl Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]CC)C(=CC=1)Cl BOBWOVWNFFQTDS-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- BZOCFPMNTFJZTG-UHFFFAOYSA-N aminoazanium;phosphate Chemical compound [NH3+]N.[NH3+]N.[NH3+]N.[O-]P([O-])([O-])=O BZOCFPMNTFJZTG-UHFFFAOYSA-N 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 230000003340 mental Effects 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003891 oxalate salts Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- VIYKYVYAKVNDPS-HKGPVOKGSA-N (2S)-2-azanyl-3-[3,4-bis(oxidanyl)phenyl]propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1.OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 VIYKYVYAKVNDPS-HKGPVOKGSA-N 0.000 description 1
- STHKCLFVJLLODK-UHFFFAOYSA-N (3-methylphenyl) benzenesulfonate Chemical compound CC1=CC=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 STHKCLFVJLLODK-UHFFFAOYSA-N 0.000 description 1
- YBPXHGRYXAFTGI-UHFFFAOYSA-N (4-chloro-3-methylphenyl) benzenesulfonate Chemical compound C1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 YBPXHGRYXAFTGI-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-Dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- PVFSNBPKQDSTPP-UHFFFAOYSA-N 2-(methylaminomethyl)phenol Chemical compound CNCC1=CC=CC=C1O PVFSNBPKQDSTPP-UHFFFAOYSA-N 0.000 description 1
- UDXXNWDSBJINMV-UHFFFAOYSA-N 2-(methylaminomethyl)phenol;hydrochloride Chemical compound Cl.CNCC1=CC=CC=C1O UDXXNWDSBJINMV-UHFFFAOYSA-N 0.000 description 1
- BJJDPKGXTMVSKI-UHFFFAOYSA-N 3-[[amino(methyl)amino]methyl]phenol Chemical compound CN(N)CC1=CC=CC(O)=C1 BJJDPKGXTMVSKI-UHFFFAOYSA-N 0.000 description 1
- MGBKJKDRMRAZKC-UHFFFAOYSA-N 3-aminobenzene-1,2-diol Chemical compound NC1=CC=CC(O)=C1O MGBKJKDRMRAZKC-UHFFFAOYSA-N 0.000 description 1
- UOTMHAOCAJROQF-UHFFFAOYSA-N 3-bromo-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Br UOTMHAOCAJROQF-UHFFFAOYSA-N 0.000 description 1
- XVEDWUMXQCOGAE-UHFFFAOYSA-N 4-bromo-2-(methylaminomethyl)phenol Chemical compound CNCC1=CC(Br)=CC=C1O XVEDWUMXQCOGAE-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- YABHGYPDBKOQOO-UHFFFAOYSA-N 4-chloro-2-(methylaminomethyl)phenol Chemical compound CNCC1=CC(Cl)=CC=C1O YABHGYPDBKOQOO-UHFFFAOYSA-N 0.000 description 1
- 229940000681 5-Hydroxytryptophan Drugs 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan zwitterion Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229960003116 Amyl Nitrite Drugs 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N Amyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N Benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 241000283725 Bos Species 0.000 description 1
- RJKPZAUBRWDYHN-UHFFFAOYSA-N BrC1=C(C=C(C=C1)C)OS(=O)(=O)C1=CC=CC=C1 Chemical compound BrC1=C(C=C(C=C1)C)OS(=O)(=O)C1=CC=CC=C1 RJKPZAUBRWDYHN-UHFFFAOYSA-N 0.000 description 1
- FJJDEUFIQDNFST-UHFFFAOYSA-O BrC=1C=C(C[NH2+]C)C=CC=1O Chemical compound BrC=1C=C(C[NH2+]C)C=CC=1O FJJDEUFIQDNFST-UHFFFAOYSA-O 0.000 description 1
- UGCXIFALLNQTSL-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC1=C(C=CC=C1Br)C Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC1=C(C=CC=C1Br)C UGCXIFALLNQTSL-UHFFFAOYSA-N 0.000 description 1
- PDFKCCRBLOEFIC-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C)C(=CC=1)Br Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C)C(=CC=1)Br PDFKCCRBLOEFIC-UHFFFAOYSA-N 0.000 description 1
- QRXOCWQSVJBANC-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CBr)C(=CC=1)Br Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CBr)C(=CC=1)Br QRXOCWQSVJBANC-UHFFFAOYSA-N 0.000 description 1
- BXHGOICUJDVQDM-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNC)C(=CC=1)Br Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNC)C(=CC=1)Br BXHGOICUJDVQDM-UHFFFAOYSA-N 0.000 description 1
- RECXDTOUOWFOEY-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNC)C(=CC=1)Cl Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNC)C(=CC=1)Cl RECXDTOUOWFOEY-UHFFFAOYSA-N 0.000 description 1
- IBRHYTYXXMEGOD-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNCC)C(=CC=1)Cl Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(CNCC)C(=CC=1)Cl IBRHYTYXXMEGOD-UHFFFAOYSA-N 0.000 description 1
- RECXDTOUOWFOEY-UHFFFAOYSA-O C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Cl Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Cl RECXDTOUOWFOEY-UHFFFAOYSA-O 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- RUQJXWSRZHHMAZ-UHFFFAOYSA-N ClC1=C(CN(N)C)C=C(C=C1)O Chemical compound ClC1=C(CN(N)C)C=C(C=C1)O RUQJXWSRZHHMAZ-UHFFFAOYSA-N 0.000 description 1
- SFDPJCGPYZPAQA-UHFFFAOYSA-O ClC=1C=C(C[NH+](N)C)C(=CC=1)O Chemical compound ClC=1C=C(C[NH+](N)C)C(=CC=1)O SFDPJCGPYZPAQA-UHFFFAOYSA-O 0.000 description 1
- ZAEBLFKQMDEPDM-UHFFFAOYSA-N Cyclobutyl radical Chemical compound [CH]1CCC1 ZAEBLFKQMDEPDM-UHFFFAOYSA-N 0.000 description 1
- SFLSHLFXELFNJZ-MRVPVSSYSA-N L-Noradrenaline Natural products NC[C@@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-MRVPVSSYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229960002748 Norepinephrine Drugs 0.000 description 1
- RXPWVQTZHIFHTC-UHFFFAOYSA-O OC1=C(C[NH+](N)C)C=CC=C1 Chemical compound OC1=C(C[NH+](N)C)C=CC=C1 RXPWVQTZHIFHTC-UHFFFAOYSA-O 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L Potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910019023 PtO Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K Trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L Zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- JEPWKPUEACSBEI-UHFFFAOYSA-N [Cl-].BrC=1C=C(C[NH2+]C)C=CC=1O Chemical compound [Cl-].BrC=1C=C(C[NH2+]C)C=CC=1O JEPWKPUEACSBEI-UHFFFAOYSA-N 0.000 description 1
- WLFYTLCGTOGALL-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C(C)C)C=CC=1 Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C(C)C)C=CC=1 WLFYTLCGTOGALL-UHFFFAOYSA-N 0.000 description 1
- JDEMAOQFOSZQGM-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Cl Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C(=CC=1)Cl JDEMAOQFOSZQGM-UHFFFAOYSA-N 0.000 description 1
- DNYAUBWFZQOXQF-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C=CC=1Br Chemical compound [Cl-].C1(=CC=CC=C1)S(=O)(=O)OC=1C=C(C[NH2+]C)C=CC=1Br DNYAUBWFZQOXQF-UHFFFAOYSA-N 0.000 description 1
- KTAWLHFAJXVBIE-UHFFFAOYSA-N [Cl-].ClC=1C=C(C[NH2+]C)C(=CC=1)O Chemical compound [Cl-].ClC=1C=C(C[NH2+]C)C(=CC=1)O KTAWLHFAJXVBIE-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920002892 amber Polymers 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-O amino(methyl)azanium Chemical compound CN[NH3+] HDZGCSFEDULWCS-UHFFFAOYSA-O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000630 rising Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011778 trisodium citrate Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE613443A true BE613443A (fi) |
Family
ID=193259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE613443D BE613443A (fi) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE613443A (fi) |
-
0
- BE BE613443D patent/BE613443A/fr unknown
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