ES2103681B1 - PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. - Google Patents

PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE.

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Publication number
ES2103681B1
ES2103681B1 ES9501815A ES9501815A ES2103681B1 ES 2103681 B1 ES2103681 B1 ES 2103681B1 ES 9501815 A ES9501815 A ES 9501815A ES 9501815 A ES9501815 A ES 9501815A ES 2103681 B1 ES2103681 B1 ES 2103681B1
Authority
ES
Spain
Prior art keywords
phenyl
methyl
propylamine
product
ethyl
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
ES9501815A
Other languages
Spanish (es)
Other versions
ES2103681A1 (en
Inventor
Flavia Arce
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 ES9501815A priority Critical patent/ES2103681B1/en
Publication of ES2103681A1 publication Critical patent/ES2103681A1/en
Application granted granted Critical
Publication of ES2103681B1 publication Critical patent/ES2103681B1/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: A) HACER REACCIONAR 3-FENIL-3-HIDROXIPROPIONATO DE ETILO CON METILAMINA PARA DAR N-METIL-3-FENIL-3-HIDROXIPROPANAMIDA; B) REDUCIR ESTE COMPUESTO CON HIDRURO DE LITIO Y ALUMINIO PARA DAR N-METIL-3-FENIL-3-HIDROXIPROPILAMINA; C) HACER REACCIONAR EN DIMETILACETAMIDA, CANTIDADES APROXIMADAMENTE EQUIMOLARES DEL PRODUCTO ANTERIOR, HIDRURO SODICO Y 1-CLORO-4-(TRIFLUOROMETIL)BENCENO, PARA FORMAR EL PRODUCTO DEL TITULO (I); Y D) OPCIONALMENTE, CONVERTIR EL PRODUCTO (I) ASI FORMADO EN SU HIDROCLORURO MEDIANTE LA ADICION DE CLORURO DE HIDROGENO. EL 3-FENIL-3-HIDROXIPROPIONATO DE ETILO DE PARTIDA SE OBTIENE POR CONDENSACION ENTRE BENZALDEHIDO Y ACETATO DE ETILO EN PRESENCIA DE UNA BASE FUERTE, PREFERIBLEMENTE BISTRIMETILSILILAMIDURO DE LITIO. LA INVENCION TIENE UTILIDAD PARA LA PREPARACION INDUSTRIALMENTE VENTAJOSA DE (1).PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. IT CONSISTS OF THE FOLLOWING STAGES: A) REACT ETHYL 3-PHENYL-3-HYDROXYPROPIONATE WITH METHYLAMINE TO GIVE N-METHYL-3-PHENYL-3-HYDROXYPROPANAMIDE; B) REDUCE THIS COMPOUND WITH LITHIUM AND ALUMINUM HYDRIDE TO GIVE N-METHYL-3-PHENYL-3-HYDROXYPROPYLAMINE; C) REACTION IN DIMETHYLACETAMIDE, QUANTITIES APPROXIMATELY EQUIMOLAR OF THE PREVIOUS PRODUCT, SODIUM HYDRIDE AND 1-CHLORINE-4- (TRIFLUOROMETIL) BENZENE, TO FORM THE PRODUCT OF TITLE (I); AND D) OPTIONALLY, CONVERT THE PRODUCT (I) SO FORMED INTO ITS HYDROCHLORIDE THROUGH THE ADDITION OF HYDROGEN CHLORIDE. STARTING ETHYL 3-PHENYL-3-HYDROXYPROPIONATE IS OBTAINED BY CONDENSATION BETWEEN BENZALDEHYDE AND ETHYL ACETATE IN THE PRESENCE OF A STRONG BASE, PREFERABLY BISTRIMETILSYLILAMIDIDE OF LITHIUM. THE INVENTION IS USEFUL FOR THE INDUSTRIAL ADVANTAGEOUS PREPARATION OF (1).

ES9501815A 1995-09-19 1995-09-19 PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. Expired - Fee Related ES2103681B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9501815A ES2103681B1 (en) 1995-09-19 1995-09-19 PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9501815A ES2103681B1 (en) 1995-09-19 1995-09-19 PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE.

Publications (2)

Publication Number Publication Date
ES2103681A1 ES2103681A1 (en) 1997-09-16
ES2103681B1 true ES2103681B1 (en) 1998-04-01

Family

ID=8291611

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9501815A Expired - Fee Related ES2103681B1 (en) 1995-09-19 1995-09-19 PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE.

Country Status (1)

Country Link
ES (1) ES2103681B1 (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
ES2103681A1 (en) 1997-09-16

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