SU618035A3 - Способ получени -диарил- (трет.-амино)-пропанола - Google Patents
Способ получени -диарил- (трет.-амино)-пропанолаInfo
- Publication number
- SU618035A3 SU618035A3 SU752159077A SU2159077A SU618035A3 SU 618035 A3 SU618035 A3 SU 618035A3 SU 752159077 A SU752159077 A SU 752159077A SU 2159077 A SU2159077 A SU 2159077A SU 618035 A3 SU618035 A3 SU 618035A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- solution
- tert
- added
- magnesium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 20
- 239000000243 solution Substances 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 11
- 229910052749 magnesium Inorganic materials 0.000 claims 11
- 239000011777 magnesium Substances 0.000 claims 11
- 239000011541 reaction mixture Substances 0.000 claims 11
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims 10
- 239000007864 aqueous solution Substances 0.000 claims 8
- 239000013078 crystal Substances 0.000 claims 8
- -1 alkyl anisole Chemical compound 0.000 claims 7
- 238000010992 reflux Methods 0.000 claims 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- 238000009835 boiling Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 4
- 239000012259 ether extract Substances 0.000 claims 4
- 238000001704 evaporation Methods 0.000 claims 4
- 230000008020 evaporation Effects 0.000 claims 4
- 229940072033 potash Drugs 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 235000015320 potassium carbonate Nutrition 0.000 claims 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000003208 petroleum Substances 0.000 claims 3
- 238000001665 trituration Methods 0.000 claims 3
- 239000007818 Grignard reagent Substances 0.000 claims 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000004795 grignard reagents Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims 2
- YGNPTIBVNPDWPS-UHFFFAOYSA-N 1-bromo-2-methoxy-3-methyl-5-(2-methylpentan-2-yl)benzene Chemical compound CCCC(C)(C)C1=CC(C)=C(OC)C(Br)=C1 YGNPTIBVNPDWPS-UHFFFAOYSA-N 0.000 claims 1
- CALWRWLFQOSHNJ-UHFFFAOYSA-N 1-bromo-4-methoxy-2,3,5,6-tetramethylbenzene Chemical compound COC1=C(C)C(C)=C(Br)C(C)=C1C CALWRWLFQOSHNJ-UHFFFAOYSA-N 0.000 claims 1
- PCZIBDAMFBPGOY-UHFFFAOYSA-N 1-phenylpropan-1-one piperidine Chemical compound C(C)C(=O)C1=CC=CC=C1.N1CCCCC1 PCZIBDAMFBPGOY-UHFFFAOYSA-N 0.000 claims 1
- KBJMBOZJLNXKDI-UHFFFAOYSA-N 2-bromo-4-tert-butyl-1-methoxybenzene Chemical compound COC1=CC=C(C(C)(C)C)C=C1Br KBJMBOZJLNXKDI-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- PPBFJCWDVJEYCW-UHFFFAOYSA-N 5-bromo-2-methoxy-1,3-di(propan-2-yl)benzene Chemical compound COC1=C(C(C)C)C=C(Br)C=C1C(C)C PPBFJCWDVJEYCW-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- GIXJCFSCLYLXMD-UHFFFAOYSA-N 6-bromo-7,8-dimethyl-3,4-dihydro-2h-chromene Chemical compound O1CCCC2=C1C(C)=C(C)C(Br)=C2 GIXJCFSCLYLXMD-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 241000209761 Avena Species 0.000 claims 1
- 235000007319 Avena orientalis Nutrition 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100314142 Mus musculus Tnik gene Proteins 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- DXVQSHRBALIFBC-UHFFFAOYSA-N 3-phenoxypropan-1-amine Chemical class NCCCOC1=CC=CC=C1 DXVQSHRBALIFBC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical class CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2508203A DE2508203C2 (de) | 1975-02-26 | 1975-02-26 | Verwendung von mehrfach substituierten α,α-Diphenyl-β-(tert.-amino)-propanolen bei der saluretischen Therapie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU618035A3 true SU618035A3 (ru) | 1978-07-30 |
Family
ID=5939810
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752159077A SU618035A3 (ru) | 1975-02-26 | 1975-07-22 | Способ получени -диарил- (трет.-амино)-пропанола |
| SU762355956A SU614093A1 (ru) | 1975-02-26 | 1976-05-11 | Многократнозамещенные диарил- -(трет.амино)пропанолы, про вл ющие диуретическое и салуретическое действие |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762355956A SU614093A1 (ru) | 1975-02-26 | 1976-05-11 | Многократнозамещенные диарил- -(трет.амино)пропанолы, про вл ющие диуретическое и салуретическое действие |
Country Status (14)
-
1975
- 1975-02-26 DE DE2508203A patent/DE2508203C2/de not_active Expired
- 1975-06-17 YU YU01825/75A patent/YU182575A/xx unknown
- 1975-07-10 LU LU72953A patent/LU72953A1/xx unknown
- 1975-07-10 NO NO752485A patent/NO142908C/no unknown
- 1975-07-11 HU HU75TE00000831A patent/HU171369B/hu unknown
- 1975-07-15 NZ NZ178112A patent/NZ178112A/xx unknown
- 1975-07-18 FI FI752082A patent/FI752082A7/fi not_active Application Discontinuation
- 1975-07-18 IE IE1613/75A patent/IE42439B1/en unknown
- 1975-07-21 CS CS755150A patent/CS194723B2/cs unknown
- 1975-07-21 RO RO7582915A patent/RO70352A/ro unknown
- 1975-07-22 SU SU752159077A patent/SU618035A3/ru active
- 1975-07-28 MX MX75100032U patent/MX3548E/es unknown
- 1975-08-13 PL PL1975182711A patent/PL101806B1/pl unknown
-
1976
- 1976-02-25 EG EG111/76A patent/EG12529A/xx active
- 1976-05-11 SU SU762355956A patent/SU614093A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| LU72953A1 (enrdf_load_stackoverflow) | 1976-02-04 |
| HU171369B (hu) | 1977-12-28 |
| NZ178112A (en) | 1978-04-28 |
| DE2508203C2 (de) | 1984-03-01 |
| PL101806B1 (pl) | 1979-02-28 |
| CS194723B2 (en) | 1979-12-31 |
| IE42439L (en) | 1976-08-26 |
| YU182575A (en) | 1982-02-28 |
| SU614093A1 (ru) | 1978-07-05 |
| RO70352A (ro) | 1982-02-26 |
| NO142908C (no) | 1980-11-12 |
| NO752485L (enrdf_load_stackoverflow) | 1976-08-27 |
| FI752082A7 (enrdf_load_stackoverflow) | 1976-08-27 |
| NO142908B (no) | 1980-08-04 |
| DE2508203A1 (de) | 1976-09-09 |
| EG12529A (en) | 1979-12-31 |
| MX3548E (es) | 1981-02-19 |
| IE42439B1 (en) | 1980-08-13 |
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