ES2103680B1 - PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. - Google Patents
PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE.Info
- Publication number
- ES2103680B1 ES2103680B1 ES9501582A ES9501582A ES2103680B1 ES 2103680 B1 ES2103680 B1 ES 2103680B1 ES 9501582 A ES9501582 A ES 9501582A ES 9501582 A ES9501582 A ES 9501582A ES 2103680 B1 ES2103680 B1 ES 2103680B1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- reaction
- preparation
- transform
- trifluoromethylphenoxy
- 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
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 ALCOHOL BENCILICO CON HIDRURO SODICO EN DIMETILACETAMIDA PRIMERO, Y CON 1-CLORO-4-(TRIFLUOROMETIL)BENCENO DESPUES, PARA OBTENER BENCIL P-TRIFLUOROMETILFENIL ETER; TRANSFORMAR ESTE EN 4-FENIL-4-(PTRIFLUOROMETILFENOXI)BUTENO POR REACCION CON EL REACTIVO N-BUTILLITIO/TETRAMETILETILENDIAMINA PRIMERO, Y CON BROMURO DE ALILO DESPUES; TRANSFORMAR EL PRODUCTO OBTENIDO EN 3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPANAL MEDIANTE REACCION DE OZONOLISIS; 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 IN 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).PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. CONSISTS OF THE FOLLOWING STAGES: REACTION WITH BENZYL ALCOHOL WITH SODIUM HYDRIDE IN DIMETHYLACETAMIDE FIRST, AND WITH 1-CHLORINE-4- (TRIFLUOROMETHYL) BENZENE THEN, TO OBTAIN BENCIL P-TRIFLUOROMEYLPHENYL; TRANSFORM THIS INTO 4-PHENYL-4- (PTRIFLUOROMETILFENOXI) BUTENE BY REACTION WITH THE N-BUTYLLITHIUM / TETRAMETILETILENDIAMINE REAGENT FIRST, AND WITH ALYL BROMIDE THEN; TRANSFORM THE PRODUCT OBTAINED IN 3-PHENYL-3- (P-TRIFLUOROMETILFENOXI) PROPANAL THROUGH OZONOLYSIS REACTION; TRANSFORM THE PRODUCT OBTAINED IN PRODUCT (I) OF THE TITLE BY REACTION WITH METHYLAMINE IN CONDITIONS OF FORMATION OF THE CORRESPONDING IMINA, AND SUBSEQUENT REDUCTION OF THE IMINA FORMED, THROUGH SODIUM CYANOBOROHIDRIDE. FINALLY THE PRODUCT (I) IS TRANSFORMED INTO ITS HYDROCHLORIDE THROUGH THE ADDITION OF HYDROGEN CHLORIDE. THE INVENTION IS USEFUL FOR THE INDUSTRIAL ADVANTAGEOUS PREPARATION OF (I).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9501582A ES2103680B1 (en) | 1995-08-03 | 1995-08-03 | PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9501582A ES2103680B1 (en) | 1995-08-03 | 1995-08-03 | PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2103680A1 ES2103680A1 (en) | 1997-09-16 |
ES2103680B1 true ES2103680B1 (en) | 1998-04-01 |
Family
ID=8291286
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9501582A Expired - Fee Related ES2103680B1 (en) | 1995-08-03 | 1995-08-03 | PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. |
Country Status (1)
Country | Link |
---|---|
ES (1) | ES2103680B1 (en) |
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 (en) * | 1986-06-13 | 1987-07-16 | Inke Sa | N-Methyl tri:fluoro:methyl-phenoxy phenyl-propylamine prepn. |
IT1228209B (en) * | 1989-01-10 | 1991-06-05 | Grato Magnone | PROCEDURE FOR THE PREPARATION OF FLUOXETINE HYDROCHLORIDE. |
FI81083C (en) * | 1989-03-03 | 1990-09-10 | Orion Yhtymae Oy | ETT FOERBAETTRAT FOERFARANDE FOER FRAMSTAELLNING AV N-METHYL-3- (P-TRIFLUORMETHYLPHENOXY) -3-PHENYLPROPYLAMINE HYDROCHLORIDE. |
IL99316A (en) * | 1991-08-27 | 1995-03-15 | Teva Pharma | Production of fluoxetine and new intermediates |
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
- 1995-08-03 ES ES9501582A patent/ES2103680B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2103680A1 (en) | 1997-09-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EC2A | Search report published |
Date of ref document: 19970916 Kind code of ref document: A1 Effective date: 19970916 |
|
FD1A | Patent lapsed |
Effective date: 20060804 |