ES2101654A1 - Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometil-fenoxi) propilamina. - Google Patents
Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometil-fenoxi) propilamina.Info
- Publication number
- ES2101654A1 ES2101654A1 ES09501492A ES9501492A ES2101654A1 ES 2101654 A1 ES2101654 A1 ES 2101654A1 ES 09501492 A ES09501492 A ES 09501492A ES 9501492 A ES9501492 A ES 9501492A ES 2101654 A1 ES2101654 A1 ES 2101654A1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- propylamine
- methyl
- trifluoromethyl
- preparation
- 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.)
- Granted
Links
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- HILDHWAXSORHRZ-UHFFFAOYSA-N 3-hydroxy-3-phenylpropionitrile Chemical compound N#CCC(O)C1=CC=CC=C1 HILDHWAXSORHRZ-UHFFFAOYSA-N 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- PHIYHIOQVWTXII-UHFFFAOYSA-N 3-amino-1-phenylpropan-1-ol Chemical compound NCCC(O)C1=CC=CC=C1 PHIYHIOQVWTXII-UHFFFAOYSA-N 0.000 abstract 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- WIQRCHMSJFFONW-UHFFFAOYSA-N norfluoxetine Chemical compound C=1C=CC=CC=1C(CCN)OC1=CC=C(C(F)(F)F)C=C1 WIQRCHMSJFFONW-UHFFFAOYSA-N 0.000 abstract 1
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 abstract 1
- -1 sodium 3-phenyl-3-hydroxy propanamine alkoxide Chemical class 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCEDIMIENTO DE PREPARACION DE N-METIL-3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPILAMINA. CONSTA DE LAS SIGUIENTES ETAPAS: A) TRANSFORMAR CIANOMETIL FENIL CETONA EN 3-FENIL-3-HIDROXIPROPANONITRILO MEDIANTE REDUCCION CON BOROHIDRURO SODICO EN TETRAHIDROFURANO; B) TRANSFORMAR 3-FENIL-3-HIDROXIPROPANONITRILO EN 3-FENIL-3-HIDROXIPROPANAMINA MEDIANTE TRATAMIENTO CON EL COMPLEJO BORANO-SULFURO DE DIMETILO; GENERAR EL ALCOXIDO SODICO DE 3-FENIL-3-HIDROXIPROPANAMINA CON HIDRURO SODICO EN DIMETILSULFOXIDO, Y HACERLO REACCIONAR CVAIN SITU CON 1-CLORO-4-(TRIFLUOROMETIL)-BENCENO; HACER REACCIONAR EL 3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPILAMINA ASI OBTENIDO, O SU HDIROCLORURO, CON CLOROFORMIATO DE METILO, FORMANDO EL CORRESPONDIENTE CARBAMATO; TRANSFORMAR CVAIN SITU DICHO CARBAMATO; EN EL PRODUCTO N-METIL-3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPILAMINA (I) DESEADO, MEDIANTE REDUCCION CON HIDRURO DE ALUMINIO Y LITIO EN TETRAHIDROFURANO. LA INVENCION TIENE UTILIDAD PARA LA PREPARACION INDUSTRIALMENTE VENTAJOSA DE (I).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9501492A ES2101654B1 (es) | 1995-07-24 | 1995-07-24 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9501492A ES2101654B1 (es) | 1995-07-24 | 1995-07-24 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2101654A1 true ES2101654A1 (es) | 1997-07-01 |
ES2101654B1 ES2101654B1 (es) | 1998-01-16 |
Family
ID=8291152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9501492A Expired - Fee Related ES2101654B1 (es) | 1995-07-24 | 1995-07-24 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Country Status (1)
Country | Link |
---|---|
ES (1) | ES2101654B1 (es) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES433720A1 (es) * | 1974-01-10 | 1976-12-01 | Lilly Co Eli | Un procedimiento para preparar los compuestos 3-ariloxi-3- fenilpropilamina. |
ES8707175A1 (es) * | 1986-06-13 | 1987-07-16 | Inke Sa | Procedimiento para la obtencion de la n-metil-3-(p-trifluorometilfenoxi)-3-fenilpropilamina |
EP0369685A2 (en) * | 1988-11-14 | 1990-05-23 | Eli Lilly And Company | Fluoxetine analog |
EP0380924A1 (en) * | 1989-01-10 | 1990-08-08 | Grato Magnone | Process for the preparation of fluoxetine hydrochloride |
EP0391070A1 (en) * | 1989-03-03 | 1990-10-10 | Orion-Yhtymä Oy Fermion | Process for the preparation of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenyl-propylamine and their salts |
WO1994000416A1 (en) * | 1992-06-26 | 1994-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof |
-
1995
- 1995-07-24 ES ES9501492A patent/ES2101654B1/es not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES433720A1 (es) * | 1974-01-10 | 1976-12-01 | Lilly Co Eli | Un procedimiento para preparar los compuestos 3-ariloxi-3- fenilpropilamina. |
ES8707175A1 (es) * | 1986-06-13 | 1987-07-16 | Inke Sa | Procedimiento para la obtencion de la n-metil-3-(p-trifluorometilfenoxi)-3-fenilpropilamina |
EP0369685A2 (en) * | 1988-11-14 | 1990-05-23 | Eli Lilly And Company | Fluoxetine analog |
EP0380924A1 (en) * | 1989-01-10 | 1990-08-08 | Grato Magnone | Process for the preparation of fluoxetine hydrochloride |
EP0391070A1 (en) * | 1989-03-03 | 1990-10-10 | Orion-Yhtymä Oy Fermion | Process for the preparation of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenyl-propylamine and their salts |
WO1994000416A1 (en) * | 1992-06-26 | 1994-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof |
Also Published As
Publication number | Publication date |
---|---|
ES2101654B1 (es) | 1998-01-16 |
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Legal Events
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EC2A | Search report published |
Date of ref document: 19970701 Kind code of ref document: A1 Effective date: 19970701 |
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FD1A | Patent lapsed |
Effective date: 20060725 |