KR870000183B1 - 페닐알킬아민의 제조방법 - Google Patents

Info

Publication number

KR870000183B1

KR870000183B1 KR1019810004912A KR810004912A KR870000183B1 KR 870000183 B1 KR870000183 B1 KR 870000183B1 KR 1019810004912 A KR1019810004912 A KR 1019810004912A KR 810004912 A KR810004912 A KR 810004912A KR 870000183 B1 KR870000183 B1 KR 870000183B1

Authority

KR

South Korea

Prior art keywords

group

carbon atoms

phenyl

amino

alkyl

Prior art date

1980-12-10

Links

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• 238000000034 method Methods 0.000 title claims description 202
• 238000002360 preparation method Methods 0.000 title description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 30
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 21
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 20
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims description 278
• -1 phenylalkyl amine Chemical class 0.000 claims description 218
• 125000004432 carbon atom Chemical group C* 0.000 claims description 204
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• 239000012279 sodium borohydride Substances 0.000 claims description 103
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 103
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 82
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 51
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 239000012280 lithium aluminium hydride Substances 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 239000002904 solvent Substances 0.000 claims description 37
• 125000003277 amino group Chemical group 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 239000011541 reaction mixture Substances 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 24
• 229910052731 fluorine Inorganic materials 0.000 claims description 24
• 150000001721 carbon Chemical group 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 210000001072 colon Anatomy 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
• 150000004678 hydrides Chemical class 0.000 claims description 17
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 14
• 239000002585 base Substances 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 230000001681 protective effect Effects 0.000 claims description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 239000011737 fluorine Substances 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
• 238000009835 boiling Methods 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 238000006722 reduction reaction Methods 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• 125000004434 sulfur atom Chemical group 0.000 claims description 11
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 10
• 229910052987 metal hydride Inorganic materials 0.000 claims description 10
• 150000004681 metal hydrides Chemical class 0.000 claims description 10
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
• 230000003287 optical effect Effects 0.000 claims description 9
• 241000282472 Canis lupus familiaris Species 0.000 claims description 8
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 239000003638 chemical reducing agent Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• 125000000732 arylene group Chemical group 0.000 claims description 6
• 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
• 235000019253 formic acid Nutrition 0.000 claims description 6
• 238000005984 hydrogenation reaction Methods 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 238000007254 oxidation reaction Methods 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 5
• 238000005695 dehalogenation reaction Methods 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 239000003513 alkali Substances 0.000 claims description 4
• 230000002152 alkylating effect Effects 0.000 claims description 4
• 230000029936 alkylation Effects 0.000 claims description 4
• 238000005804 alkylation reaction Methods 0.000 claims description 4
• 230000000269 nucleophilic effect Effects 0.000 claims description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000001299 aldehydes Chemical class 0.000 claims description 3
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 230000001590 oxidative effect Effects 0.000 claims description 3
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
• 238000007069 methylation reaction Methods 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
• 230000035479 physiological effects, processes and functions Effects 0.000 claims description 2
• 150000003138 primary alcohols Chemical class 0.000 claims description 2
• 150000003333 secondary alcohols Chemical class 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims 6
• 125000003884 phenylalkyl group Chemical group 0.000 claims 3
• 125000006239 protecting group Chemical group 0.000 claims 3
• SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims 2
• 230000010933 acylation Effects 0.000 claims 1
• 238000005917 acylation reaction Methods 0.000 claims 1
• 229910052783 alkali metal Inorganic materials 0.000 claims 1
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
• 150000008051 alkyl sulfates Chemical class 0.000 claims 1
• ZGFPIGGZMWGPPW-UHFFFAOYSA-N formaldehyde;formic acid Chemical compound O=C.OC=O ZGFPIGGZMWGPPW-UHFFFAOYSA-N 0.000 claims 1
• 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
• 150000004692 metal hydroxides Chemical class 0.000 claims 1
• 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims 1
• 229910052757 nitrogen Inorganic materials 0.000 claims 1
• 229910021653 sulphate ion Inorganic materials 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 603
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract description 20
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 14
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
• 125000001475 halogen functional group Chemical group 0.000 abstract 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
• 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 abstract 1
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 522
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 255
• 238000002329 infrared spectrum Methods 0.000 description 137
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 127
• 238000002211 ultraviolet spectrum Methods 0.000 description 126
• 239000003921 oil Substances 0.000 description 103
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 88
• 238000002844 melting Methods 0.000 description 80
• 230000008018 melting Effects 0.000 description 80
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 67
• 239000000243 solution Substances 0.000 description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
• 125000003118 aryl group Chemical group 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 38
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 37
• 125000001931 aliphatic group Chemical group 0.000 description 37
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• 238000000354 decomposition reaction Methods 0.000 description 25
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 24
• 239000003480 eluent Substances 0.000 description 23
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 238000003756 stirring Methods 0.000 description 21
• 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 19
• 239000011734 sodium Substances 0.000 description 19
• 229910052708 sodium Inorganic materials 0.000 description 19
• 239000000203 mixture Substances 0.000 description 18
• 238000001704 evaporation Methods 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 150000003254 radicals Chemical class 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 15
• 230000008020 evaporation Effects 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 14
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• 229930040373 Paraformaldehyde Natural products 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
• 238000001816 cooling Methods 0.000 description 12
• 229920002866 paraformaldehyde Polymers 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• ATKJJUFAWYSFID-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-bromoethanone Chemical compound NC1=C(Cl)C=C(C(=O)CBr)C=C1Cl ATKJJUFAWYSFID-UHFFFAOYSA-N 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 11
• 229910021529 ammonia Inorganic materials 0.000 description 11
• ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 239000012362 glacial acetic acid Substances 0.000 description 8
• QSUCCPHDCQKGPA-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)Cl)O)Cl QSUCCPHDCQKGPA-UHFFFAOYSA-N 0.000 description 7
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• XETXTUWQXVYELX-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)C(C)C)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)C(C)C)O)Cl XETXTUWQXVYELX-UHFFFAOYSA-N 0.000 description 7
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 7
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
• 239000012074 organic phase Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• JLPKZJDZXIKSCP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=C(N)C(Cl)=C1 JLPKZJDZXIKSCP-UHFFFAOYSA-N 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
• 229910010277 boron hydride Inorganic materials 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 229960004132 diethyl ether Drugs 0.000 description 6
• DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• IKYFHRVPKIFGMH-UHFFFAOYSA-N 1-phenoxypropan-2-amine Chemical compound CC(N)COC1=CC=CC=C1 IKYFHRVPKIFGMH-UHFFFAOYSA-N 0.000 description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 230000036772 blood pressure Effects 0.000 description 5
• MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
• 239000002808 molecular sieve Substances 0.000 description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• PJKGAXBXMOOWRN-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-fluorophenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)F)O)Cl PJKGAXBXMOOWRN-UHFFFAOYSA-N 0.000 description 4
• UHXHHIAYNSRNOI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-methylpropan-1-amine Chemical compound CNCCCC1=CC=C(OC)C=C1 UHXHHIAYNSRNOI-UHFFFAOYSA-N 0.000 description 4
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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