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.

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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
Application number
ES9501582A
Other languages
Spanish (es)
Other versions
ES2103680A1 (en
Inventor
Carmen Dominguez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lilly SA
Original Assignee
Lilly SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lilly SA filed Critical Lilly SA
Priority to ES9501582A priority Critical patent/ES2103680B1/en
Publication of ES2103680A1 publication Critical patent/ES2103680A1/en
Application granted granted Critical
Publication of ES2103680B1 publication Critical patent/ES2103680B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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  • 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).

ES9501582A 1995-08-03 1995-08-03 PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. Expired - Fee Related ES2103680B1 (en)

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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
ES2103680A1 (en) 1997-09-16

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