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EP1836185A1 - Procede de purification de (1s)-3-methylamino-1-(2-thienyl)-1-propanol - Google Patents

Procede de purification de (1s)-3-methylamino-1-(2-thienyl)-1-propanol

Info

Publication number
EP1836185A1
EP1836185A1 EP05820701A EP05820701A EP1836185A1 EP 1836185 A1 EP1836185 A1 EP 1836185A1 EP 05820701 A EP05820701 A EP 05820701A EP 05820701 A EP05820701 A EP 05820701A EP 1836185 A1 EP1836185 A1 EP 1836185A1
Authority
EP
European Patent Office
Prior art keywords
thienyl
propanol
methylamino
distillation
purifying
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.)
Withdrawn
Application number
EP05820701A
Other languages
German (de)
English (en)
Inventor
Rainer STÜRMER
Jürgen Däuwel
Maria Kesseler
Brigitte Achatz
Michael Breuer
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1836185A1 publication Critical patent/EP1836185A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/12—Molecular distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Definitions

  • the present invention relates to a process for purifying (1S) -3-methylamino-1- (2-thienyl) -1-propanol.
  • (1S) -3-methylamino-1- (2-thienyl) -1-propanol is an important intermediate for the preparation of medicaments, in particular of duloxetine ®, an active pharmaceutical ingredient of EIiLiIIy & Co, USA.
  • WO 2004/031168 likewise describes the preparation of (1S) -3-methylamino-1- (2-thienyl) -1-propanol.
  • the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol is also carried out here by crystallization from methyl tert-butyl ether.
  • WO 2004/005307 likewise describes the preparation of (1S) -3-methylamino-1- (2-thienyl) -1-propanol.
  • the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol is also carried out here by crystallization from methyl tert-butyl ether.
  • the object was to provide a purification process for (1S) -3-methylamino-1- (2-thienyl) -1-propanol, which provides the desired product both in high chemical and enantiomeric purity as well as in a high yield and also in the technical scale should be feasible at reasonable cost.
  • This object is achieved by a process for purifying (1S) -3-methylamino-1- (2-thienyl) -1-propanol by distillation of a reaction mixture containing between 25 and 99% by weight of (1S) -3-methylamino -1- (2-thienyl) -1-propanol.
  • reaction mixture is intended to have the following meaning: it may be the non-purified mixture from the reaction for the preparation of (1S) -3-methylamino-1- (2-thienyl) -1-propanol, so for example to the Reaction mixture of methylamine and (1S) -3-chloro-1- (2-thienyl) -1-propanol, but depending on the preparation route, it is also possible for (1S) -3-methylamino-1- (2- thienyl) -1-propanol - a mixture of other reactants, but the term “reaction mixture” also includes the purified or partially purified reaction product (1S) -3-methylamino-1- (2-thienyl) -1- propanol.
  • a solution of (1S) -3-methylamino-1- (2-thienyl) -1-propanol in one or more solvents is intended to be a "reaction mixture containing ((1S) -3-methylamino-1- (2-thienyl) -1-propanol contains "to be understood.
  • the reaction mixture contains the valuable substance (1S) -3-methylamino-1- (2-thienyl) -1-propanol usually in an amount of 25 to 99 wt .-%, preferably from 40 to 98 wt .-%, particularly preferably in in an amount of more than 50% by weight.
  • the (1S) -3-methylamino-1- (2-thienyl) -1-propanol is present in an amount of less than 25% by weight in the reaction mixture, it is customary to recommend a concentration step before the distillation, for example the removal of solvents or enriching (1S) -3-methylamino-1- (2-thienyl) -1-propanol by extraction.
  • concentration step for example the removal of solvents or enriching (1S) -3-methylamino-1- (2-thienyl) -1-propanol by extraction.
  • the distillation can be carried out in a variety of configurations known to those skilled in the art, as described in detail in, for example, chemical engineering manuals such as Ulimann or Winnacker-Kuchler.
  • Particularly preferred embodiments of the method according to the invention are so-called short-path or molecular distillation, in which work is carried out as short as possible and rectilinear paths between the evaporator and condenser surfaces.
  • the inventive method allows the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol in unexpectedly high chemical yield while high purity in a single operation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

La présente invention concerne un procédé de purification de (1S)-3-méthylamino-1-(2-thiényl)-1-propanol par distillation d'un mélange réactionnel contenant entre 25 et 99 % en poids de (1S)-3-méthylamino-1-(2-thiényl)-1-propanol.
EP05820701A 2005-01-05 2005-12-31 Procede de purification de (1s)-3-methylamino-1-(2-thienyl)-1-propanol Withdrawn EP1836185A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005000867A DE102005000867A1 (de) 2005-01-05 2005-01-05 Verfahren zur Reinigung von (1S)-3-methylamino-1-(2-thienyl)-1-propanol
PCT/EP2005/014161 WO2006072465A1 (fr) 2005-01-05 2005-12-31 Procede de purification de (1s)-3-methylamino-1-(2-thienyl)-1-propanol

Publications (1)

Publication Number Publication Date
EP1836185A1 true EP1836185A1 (fr) 2007-09-26

Family

ID=35788364

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05820701A Withdrawn EP1836185A1 (fr) 2005-01-05 2005-12-31 Procede de purification de (1s)-3-methylamino-1-(2-thienyl)-1-propanol

Country Status (7)

Country Link
US (1) US20080108835A1 (fr)
EP (1) EP1836185A1 (fr)
JP (1) JP2008526703A (fr)
CN (1) CN101098863B (fr)
CA (1) CA2590660A1 (fr)
DE (1) DE102005000867A1 (fr)
WO (1) WO2006072465A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107417663B (zh) * 2017-09-25 2019-05-28 台州职业技术学院 一种高纯(s)-3-甲基氨基-1-(噻吩-2-基)丙醇的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004031168A2 (fr) * 2002-10-07 2004-04-15 Lonza Ag Procedes et produits intermediaires pour la preparation de derives de 3-amino-1-(2-thienyl)-1-propanol optiquement actifs

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003253036A1 (en) * 2002-07-09 2004-01-23 Lonza Ag Process for the preparation of optically active 3-n-methylamino-1-(2-thienyl)-1-propanol

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004031168A2 (fr) * 2002-10-07 2004-04-15 Lonza Ag Procedes et produits intermediaires pour la preparation de derives de 3-amino-1-(2-thienyl)-1-propanol optiquement actifs

Also Published As

Publication number Publication date
US20080108835A1 (en) 2008-05-08
JP2008526703A (ja) 2008-07-24
CA2590660A1 (fr) 2006-07-13
CN101098863B (zh) 2010-09-15
DE102005000867A1 (de) 2006-07-13
CN101098863A (zh) 2008-01-02
WO2006072465A1 (fr) 2006-07-13

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Legal Events

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Owner name: BASF SE

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Effective date: 20110412