CA1041545A - Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines - Google Patents
Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolaminesInfo
- Publication number
- CA1041545A CA1041545A CA212,850A CA212850A CA1041545A CA 1041545 A CA1041545 A CA 1041545A CA 212850 A CA212850 A CA 212850A CA 1041545 A CA1041545 A CA 1041545A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- process according
- effected
- compound
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
- 239000012279 sodium borohydride Substances 0.000 claims description 9
- SAFBWLLTIPIZTP-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-2-oxoacetaldehyde;hydrate Chemical compound O.NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl SAFBWLLTIPIZTP-UHFFFAOYSA-N 0.000 claims description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 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 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- OPAPFFIFYJTRRI-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclobutylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC1CCC1)O)Cl OPAPFFIFYJTRRI-UHFFFAOYSA-N 0.000 claims 1
- GSTCQRQIQKYHLZ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclopentylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC1CCCC1)O)Cl GSTCQRQIQKYHLZ-UHFFFAOYSA-N 0.000 claims 1
- FRLAHIZRTFRSMT-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclopropylamino)ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CNC1CC1 FRLAHIZRTFRSMT-UHFFFAOYSA-N 0.000 claims 1
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 abstract 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000001766 physiological effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BCISXCSLXUAFMM-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-2-oxoacetaldehyde Chemical compound NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl BCISXCSLXUAFMM-UHFFFAOYSA-N 0.000 description 1
- -1 3,5-dichloro-phenylglyoxal hydrate Chemical compound 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940106265 charcoal Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2354959A DE2354959C3 (de) | 1973-11-02 | 1973-11-02 | Neues Verfahren zur Herstellung von 4-Amino-3,5 dihalogen phenyl-athanolaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041545A true CA1041545A (en) | 1978-10-31 |
Family
ID=5897109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA212,850A Expired CA1041545A (en) | 1973-11-02 | 1974-11-01 | Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5855133B2 (fi) |
| AT (1) | AT340394B (fi) |
| BG (1) | BG23746A3 (fi) |
| CA (1) | CA1041545A (fi) |
| CH (1) | CH609040A5 (fi) |
| CS (1) | CS175487B2 (fi) |
| DD (1) | DD116599A5 (fi) |
| DE (1) | DE2354959C3 (fi) |
| DK (1) | DK134484C (fi) |
| ES (1) | ES430587A1 (fi) |
| FI (1) | FI60858C (fi) |
| HU (1) | HU168133B (fi) |
| NL (1) | NL7414223A (fi) |
| NO (1) | NO139479C (fi) |
| PL (1) | PL96537B1 (fi) |
| RO (1) | RO68703A (fi) |
| SE (2) | SE411546B (fi) |
| SU (1) | SU549079A3 (fi) |
| YU (1) | YU36918B (fi) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017021982A1 (en) * | 2015-08-06 | 2017-02-09 | Vamsi Labs Ltd. | A PROCESS FOR PREPARING β AGONIST |
| CN111393311A (zh) * | 2020-03-30 | 2020-07-10 | 苏州弘森药业股份有限公司 | 一种盐酸克伦特罗的环保无毒合成方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3714484A1 (de) * | 1987-04-30 | 1988-11-10 | Bayer Ag | Neue aminophenylethylamin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als leistungsfoerderer |
| US5541188A (en) * | 1987-09-15 | 1996-07-30 | The Rowett Research Institute | Therapeutic applications of beta-adrenergic agonists |
| US5530029A (en) * | 1987-09-15 | 1996-06-25 | The Rowett Research Institute | Therapeutic applications of clenbuterol |
-
1973
- 1973-11-02 DE DE2354959A patent/DE2354959C3/de not_active Expired
-
1974
- 1974-09-19 FI FI2736/74A patent/FI60858C/fi active
- 1974-09-20 AT AT756374A patent/AT340394B/de not_active IP Right Cessation
- 1974-10-02 ES ES430587A patent/ES430587A1/es not_active Expired
- 1974-10-18 CS CS7165A patent/CS175487B2/cs unknown
- 1974-10-22 DK DK552274A patent/DK134484C/da active
- 1974-10-24 YU YU2850/74A patent/YU36918B/xx unknown
- 1974-10-25 SU SU2069690A patent/SU549079A3/ru active
- 1974-10-29 BG BG028068A patent/BG23746A3/xx unknown
- 1974-10-30 DD DD182043A patent/DD116599A5/xx unknown
- 1974-10-30 CH CH1454274A patent/CH609040A5/xx not_active IP Right Cessation
- 1974-10-31 PL PL1974175272A patent/PL96537B1/pl unknown
- 1974-10-31 RO RO7480380A patent/RO68703A/ro unknown
- 1974-10-31 NL NL7414223A patent/NL7414223A/xx not_active Application Discontinuation
- 1974-11-01 HU HUTO987A patent/HU168133B/hu unknown
- 1974-11-01 JP JP49126469A patent/JPS5855133B2/ja not_active Expired
- 1974-11-01 SE SE7413786A patent/SE411546B/sv not_active IP Right Cessation
- 1974-11-01 NO NO743946A patent/NO139479C/no unknown
- 1974-11-01 CA CA212,850A patent/CA1041545A/en not_active Expired
-
1977
- 1977-07-28 SE SE7708686A patent/SE430057B/xx not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017021982A1 (en) * | 2015-08-06 | 2017-02-09 | Vamsi Labs Ltd. | A PROCESS FOR PREPARING β AGONIST |
| EP3331848A4 (en) * | 2015-08-06 | 2019-07-17 | Vamsi Labs Ltd. | PROCESS FOR THE PREPARATION OF BETA AGONISTS |
| US10414717B2 (en) | 2015-08-06 | 2019-09-17 | Vamsi Lab Ltd. | Process for preparing beta agonist |
| CN111393311A (zh) * | 2020-03-30 | 2020-07-10 | 苏州弘森药业股份有限公司 | 一种盐酸克伦特罗的环保无毒合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SE411546B (sv) | 1980-01-14 |
| DE2354959B2 (de) | 1979-06-07 |
| CH609040A5 (en) | 1979-02-15 |
| DK134484B (da) | 1976-11-15 |
| DK134484C (da) | 1977-04-25 |
| NO139479B (no) | 1978-12-11 |
| SU549079A3 (ru) | 1977-02-28 |
| HU168133B (en) | 1976-02-28 |
| JPS5855133B2 (ja) | 1983-12-08 |
| PL96537B1 (pl) | 1977-12-31 |
| CS175487B2 (fi) | 1977-05-31 |
| ES430587A1 (es) | 1976-09-01 |
| DE2354959A1 (de) | 1975-05-15 |
| NL7414223A (nl) | 1975-05-07 |
| RO68703A (ro) | 1981-09-24 |
| FI60858C (fi) | 1982-04-13 |
| NO743946L (fi) | 1975-05-26 |
| YU285074A (en) | 1982-06-18 |
| FI60858B (fi) | 1981-12-31 |
| AT340394B (de) | 1977-12-12 |
| NO139479C (no) | 1979-03-21 |
| DK552274A (fi) | 1975-06-23 |
| SE7708686L (sv) | 1977-07-28 |
| FI273674A (fi) | 1975-05-03 |
| BG23746A3 (en) | 1977-10-12 |
| SE7413786L (fi) | 1975-05-05 |
| SE430057B (sv) | 1983-10-17 |
| DD116599A5 (fi) | 1975-12-05 |
| JPS5071637A (fi) | 1975-06-13 |
| ATA756374A (de) | 1977-04-15 |
| YU36918B (en) | 1984-08-31 |
| DE2354959C3 (de) | 1980-02-07 |
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