SU489308A3 - Способ получени 1-изопропиламино-3-(4-ацетамидофенокси)-2-пропанола - Google Patents
Способ получени 1-изопропиламино-3-(4-ацетамидофенокси)-2-пропанолаInfo
- Publication number
- SU489308A3 SU489308A3 SU1843736A SU1843736A SU489308A3 SU 489308 A3 SU489308 A3 SU 489308A3 SU 1843736 A SU1843736 A SU 1843736A SU 1843736 A SU1843736 A SU 1843736A SU 489308 A3 SU489308 A3 SU 489308A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetamidophenoxy
- alcohol
- propanol
- product
- isopropylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- -1 4-acetamidophenoxy Chemical group 0.000 claims description 10
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- 229940081310 piperonal Drugs 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 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
- 238000000227 grinding Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- AUDQFUJSCJUOTF-UHFFFAOYSA-N hypochlorous acid;phenol Chemical compound ClO.OC1=CC=CC=C1 AUDQFUJSCJUOTF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OQAKYHCGYGLHAZ-UHFFFAOYSA-N n-[4-(oxiran-2-ylmethoxy)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCC1OC1 OQAKYHCGYGLHAZ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001967 HU164032B (OSRAM) | 1971-11-02 | 1971-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU489308A3 true SU489308A3 (ru) | 1975-10-25 |
Family
ID=10995399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1843736A SU489308A3 (ru) | 1971-11-02 | 1972-11-01 | Способ получени 1-изопропиламино-3-(4-ацетамидофенокси)-2-пропанола |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT321894B (OSRAM) |
| CA (1) | CA976565A (OSRAM) |
| CH (1) | CH572899A5 (OSRAM) |
| CS (1) | CS173608B2 (OSRAM) |
| DD (1) | DD100460A5 (OSRAM) |
| DK (1) | DK129512B (OSRAM) |
| ES (1) | ES408190A1 (OSRAM) |
| FI (1) | FI55989C (OSRAM) |
| HU (1) | HU164032B (OSRAM) |
| PL (1) | PL82439B1 (OSRAM) |
| SE (1) | SE375986B (OSRAM) |
| SU (1) | SU489308A3 (OSRAM) |
| YU (1) | YU273072A (OSRAM) |
-
1971
- 1971-11-02 HU HUEE001967 patent/HU164032B/hu unknown
-
1972
- 1972-10-30 CH CH1579272A patent/CH572899A5/xx not_active IP Right Cessation
- 1972-10-31 PL PL15856872A patent/PL82439B1/pl unknown
- 1972-10-31 FI FI302372A patent/FI55989C/fi active
- 1972-11-01 CS CS736972A patent/CS173608B2/cs unknown
- 1972-11-01 SU SU1843736A patent/SU489308A3/ru active
- 1972-11-01 DK DK540272A patent/DK129512B/da unknown
- 1972-11-01 DD DD16662172A patent/DD100460A5/xx unknown
- 1972-11-01 CA CA155,333A patent/CA976565A/en not_active Expired
- 1972-11-01 SE SE1416572A patent/SE375986B/xx unknown
- 1972-11-02 ES ES408190A patent/ES408190A1/es not_active Expired
- 1972-11-02 YU YU273072A patent/YU273072A/xx unknown
- 1972-11-02 AT AT931572A patent/AT321894B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK129512C (OSRAM) | 1975-03-17 |
| FI55989C (fi) | 1979-11-12 |
| DD100460A5 (OSRAM) | 1973-09-20 |
| DE2253776A1 (de) | 1973-05-30 |
| PL82439B1 (OSRAM) | 1975-10-31 |
| SE375986B (OSRAM) | 1975-05-05 |
| CS173608B2 (OSRAM) | 1977-02-28 |
| YU273072A (en) | 1980-09-25 |
| AT321894B (de) | 1975-04-25 |
| ES408190A1 (es) | 1975-11-16 |
| CA976565A (en) | 1975-10-21 |
| CH572899A5 (OSRAM) | 1976-02-27 |
| DK129512B (da) | 1974-10-21 |
| DE2253776B2 (de) | 1976-03-18 |
| HU164032B (OSRAM) | 1973-12-28 |
| FI55989B (fi) | 1979-07-31 |
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