AU1908388A - New process for the enantiospecific preparation of (s)-2-ethylamino-1-(3-trifluoromethyl)phenyl)propane - Google Patents

New process for the enantiospecific preparation of (s)-2-ethylamino-1-(3-trifluoromethyl)phenyl)propane

Info

Publication number
AU1908388A
AU1908388A AU19083/88A AU1908388A AU1908388A AU 1908388 A AU1908388 A AU 1908388A AU 19083/88 A AU19083/88 A AU 19083/88A AU 1908388 A AU1908388 A AU 1908388A AU 1908388 A AU1908388 A AU 1908388A
Authority
AU
Australia
Prior art keywords
ethylamino
propane
new process
trifluoromethyl
phenyl
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.)
Granted
Application number
AU19083/88A
Other versions
AU602101B2 (en
Inventor
Alexandre Alexakis
Claude Fugier
Michel Leroux
Robert Mauge
Jean-Francois Normant
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.)
Laboratoires Servier SAS
Original Assignee
Laboratoires Servier SAS
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 Laboratoires Servier SAS filed Critical Laboratoires Servier SAS
Publication of AU1908388A publication Critical patent/AU1908388A/en
Application granted granted Critical
Publication of AU602101B2 publication Critical patent/AU602101B2/en
Assigned to LES LABORATOIRES SERVIER reassignment LES LABORATOIRES SERVIER Alteration of Name(s) in Register under S187 Assignors: ADIR ET COMPAGNIE
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

New process for the enantiospecific preparation of (S)-2-ethylamino-1-(3-trifluoromethylphenyl)propane, characterised in that benzaldehyde is condensed with (S)-alaninol and that, after reduction, the product originating from the reaction is condensed with acetaldehyde to obtain (S)-N-benzyl-N-ethyl alaninol, which is subjected to the action of thionyl chloride to give, after neutralisation, (S)-2-(N-benzyl-N-ethylamino)-1-chloropropane, which is in its turn condensed with 3-trifluoromethylphenylmagnesium bromide to give (S)-2-(N-benzyl-N-ethylamino)-1-(3-trifluoromethylphenyl)- propane which, after debenzylation by hydrogenolysis, produces (S)-2-ethylamino-1-(3-trifluoromethylphenyl)propane.
AU19083/88A 1987-07-16 1988-07-15 New process for the enantiospecific preparation of (s)-2-ethylamino-1-(3-trifluoromethyl)phenyl)propane Ceased AU602101B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8710020A FR2618148B1 (en) 1987-07-16 1987-07-16 NEW PROCESS FOR THE ENANTIOSPECIFIC PREPARATION OF ETHYLAMINO-2 (TRIFLUOROMETHYL-3 PHENYL) -1 PROPANE
FR8710020 1987-07-16

Publications (2)

Publication Number Publication Date
AU1908388A true AU1908388A (en) 1989-01-19
AU602101B2 AU602101B2 (en) 1990-09-27

Family

ID=9353184

Family Applications (1)

Application Number Title Priority Date Filing Date
AU19083/88A Ceased AU602101B2 (en) 1987-07-16 1988-07-15 New process for the enantiospecific preparation of (s)-2-ethylamino-1-(3-trifluoromethyl)phenyl)propane

Country Status (13)

Country Link
EP (1) EP0301925B1 (en)
AT (1) ATE68783T1 (en)
AU (1) AU602101B2 (en)
DE (1) DE3865765D1 (en)
DK (1) DK172313B1 (en)
ES (1) ES2009944A6 (en)
FR (1) FR2618148B1 (en)
GR (1) GR1002241B (en)
IE (1) IE59990B1 (en)
NZ (1) NZ224499A (en)
OA (1) OA08845A (en)
PT (1) PT88011B (en)
ZA (1) ZA883484B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1292595B1 (en) * 1997-06-03 1999-02-08 Alfa Chem Ital PROCESS FOR THE PRODUCTION OF DEXFENFLURAMINE HYDROCHLORIDE.
EP3170807B1 (en) 2015-11-23 2019-12-11 Frau Pharma S.r.l. New method for synthesis of fenfluramine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH204708A (en) * 1937-07-21 1939-05-15 Chem Fab Vormals Sandoz Process for the preparation of an amino alcohol.
US3198834A (en) * 1964-07-27 1965-08-03 Snc Science Union Et Compagnie Optical isomers of trifluoromethylated phenethylamines
US3792048A (en) * 1970-10-29 1974-02-12 Pacific Res Labor Process for hydrolyzing 3-trifluoromethyl phenethylamines

Also Published As

Publication number Publication date
NZ224499A (en) 1990-07-26
GR880100293A (en) 1989-04-12
EP0301925A1 (en) 1989-02-01
IE881335L (en) 1989-01-16
DE3865765D1 (en) 1991-11-28
ES2009944A6 (en) 1989-10-16
EP0301925B1 (en) 1991-10-23
DK373888D0 (en) 1988-07-05
GR1002241B (en) 1996-04-22
ZA883484B (en) 1988-11-21
IE59990B1 (en) 1994-05-18
PT88011A (en) 1989-06-30
FR2618148B1 (en) 1989-10-27
ATE68783T1 (en) 1991-11-15
AU602101B2 (en) 1990-09-27
PT88011B (en) 1995-03-01
DK373888A (en) 1989-01-17
DK172313B1 (en) 1998-03-16
FR2618148A1 (en) 1989-01-20
OA08845A (en) 1989-03-31

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Legal Events

Date Code Title Description
PC Assignment registered

Owner name: LES LABORATOIRES SERVIER

Free format text: FORMER OWNER WAS: ADIR ET CIE

MK14 Patent ceased section 143(a) (annual fees not paid) or expired