ES2101655B1 - Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. - Google Patents
Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina.Info
- Publication number
- ES2101655B1 ES2101655B1 ES9501530A ES9501530A ES2101655B1 ES 2101655 B1 ES2101655 B1 ES 2101655B1 ES 9501530 A ES9501530 A ES 9501530A ES 9501530 A ES9501530 A ES 9501530A ES 2101655 B1 ES2101655 B1 ES 2101655B1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- reaction
- methyl
- transform
- trifluorometilfe
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 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 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 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 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 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: HACER REACCIONAR BENZALDEHIDO CON BROMURO DE ALILMAGNESIO PARA OBTENER 1-FENIL-3-BUTEN-1-OL; TRANSFORMAR ESTE EN 4-FENIL-4-(P-TRIFLUOROMETILFENOXI)BUTENO POR REACCION CON 4-TRIFLUOROMETILFENOL EN PRESENCIA DE TRIFENILFOSFINA Y AZODICARBOXILATO DE DIETILO; TRANSFORMAR EL PRODUCTO OBTENIDO EN 3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPANAL MEDIANTE REACCION CON TETROXIDO DE OSMIO Y PERYODATO SODICO; TRANSFORMAR EL PRODUCTO OBTENIDO EN EL PRODUCTO (I) DEL TITULO POR REACCION CON METILAMINA EN CONDICIONES DE FORMACION DE LA CORRESPONDIENTE IMINA, Y POSTERIOR REDUCCION CVAIN SITU DE LA IMINA FORMADA, MEDIANTE CIANOBOROHIDRURO SODICO. FINALMENTE EL PRODUCTO (I) SE TRANSFORMA EN SU HIDROCLORURO MEDIANTE LA ADICION DE CLORURO DE HIDROGENO. LA INVENCION TIENE UTILIDAD PARA LA PREPARACION INDUSTRIALMENTE VENTAJOSA DE (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501530A ES2101655B1 (es) | 1995-07-28 | 1995-07-28 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501530A ES2101655B1 (es) | 1995-07-28 | 1995-07-28 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2101655A1 ES2101655A1 (es) | 1997-07-01 |
| ES2101655B1 true ES2101655B1 (es) | 1998-01-16 |
Family
ID=8291207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9501530A Expired - Fee Related ES2101655B1 (es) | 1995-07-28 | 1995-07-28 | Procedimiento de preparacion de n-metil-3-fenil-3-(p-trifluorometilfe noxi) propilamina. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2101655B1 (es) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| ES8707175A1 (es) * | 1986-06-13 | 1987-07-16 | Inke Sa | Procedimiento para la obtencion de la n-metil-3-(p-trifluorometilfenoxi)-3-fenilpropilamina |
| CA2002483C (en) * | 1988-11-14 | 1999-08-17 | Ray Ward Fuller | Fluoxetine analog |
| IT1228209B (it) * | 1989-01-10 | 1991-06-05 | Grato Magnone | Procedimento per la preparazione di fluoxetina cloridrato. |
| FI81083C (fi) * | 1989-03-03 | 1990-09-10 | Orion Yhtymae Oy | Ett foerbaettrat foerfarande foer framstaellning av n-metyl-3-(p-trifluormetylfenoxi)-3-fenylpropylamin hydroklorid. |
| HU9202128D0 (en) * | 1992-06-26 | 1992-10-28 | Richter Gedeon Vegyeszet | Method for producing n-methyl-(3-phenyl-3-(4-[trifluoro-methyl])-phenooxi-)-amine |
-
1995
- 1995-07-28 ES ES9501530A patent/ES2101655B1/es not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2101655A1 (es) | 1997-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 19970701 Kind code of ref document: A1 Effective date: 19970701 |
|
| FD1A | Patent lapsed |
Effective date: 20060729 |