ES2101655B1 - N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE. - Google Patents

N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

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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
Application number
ES9501530A
Other languages
Spanish (es)
Other versions
ES2101655A1 (en
Inventor
Almudena Rubio
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 ES9501530A priority Critical patent/ES2101655B1/en
Publication of ES2101655A1 publication Critical patent/ES2101655A1/en
Application granted granted Critical
Publication of ES2101655B1 publication Critical patent/ES2101655B1/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 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).PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. CONSISTS OF THE FOLLOWING STAGES: REACTION WITH BENZALDEHYDE WITH ALYLMAGNESIUM BROMIDE TO OBTAIN 1-FENYL-3-BUTEN-1-OL; TRANSFORM THIS INTO 4-PHENYL-4- (P-TRIFLUOROMETILFENOXI) BUTENE BY REACTION WITH 4-TRIFLUOROMETILFENOL IN THE PRESENCE OF TRIPHENYLPHOSPHINE AND DIETHYL AZODICARBOXYLATE; TRANSFORM THE PRODUCT OBTAINED IN 3-PHENYL-3- (P-TRIFLUOROMETILFENOXI) PROPANAL THROUGH REACTION WITH OSMIO TETROXIDE AND SODIUM PERYODATE; TRANSFORM THE PRODUCT OBTAINED INTO PRODUCT (I) OF THE TITLE BY REACTION WITH METHYLAMINE IN CONDITIONS OF FORMATION OF THE CORRESPONDING IMINE, AND SUBSEQUENT REDUCTION OF THE FORMED IMINE, 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).

ES9501530A 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE. Expired - Fee Related ES2101655B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9501530A ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9501530A ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Publications (2)

Publication Number Publication Date
ES2101655A1 ES2101655A1 (en) 1997-07-01
ES2101655B1 true ES2101655B1 (en) 1998-01-16

Family

ID=8291207

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9501530A Expired - Fee Related ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Country Status (1)

Country Link
ES (1) ES2101655B1 (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.
IL92245A0 (en) * 1988-11-14 1990-07-26 Lilly Co Eli Fluoxetine analog
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.
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
ES2101655A1 (en) 1997-07-01

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