EP1836185A1 - Method for purifying (1s)-3-methylamino-1-(2-thienyl)-1-propanol - Google Patents

Method for purifying (1s)-3-methylamino-1-(2-thienyl)-1-propanol

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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
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EP
European Patent Office
Prior art keywords
thienyl
propanol
methylamino
distillation
purifying
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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.)
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Application number
EP05820701A
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German (de)
French (fr)
Inventor
Rainer STÜRMER
Jürgen Däuwel
Maria Kesseler
Brigitte Achatz
Michael Breuer
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1836185A1 publication Critical patent/EP1836185A1/en
Withdrawn legal-status Critical Current

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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.

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

Abstract

The invention relates to a method for purifying (1S)-3-methylamino-1-(2-thienyl)-1-propanol by the distillation of a reaction mixture containing between 25 and 99 wt. % (1S)-3-methylamino-1-(2-thienyl)-1-propanol.

Description

Verfahren zur Reinigung von (1S)-3-methylamino-1-(2-thienyl)-1-propanolProcess for the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol
Beschreibungdescription
Die vorliegende Erfindung betrifft ein Verfahren zur Reinigung von (1S)-3-methylamino- 1 -(2-thienyl)-1 -propanol.The present invention relates to a process for purifying (1S) -3-methylamino-1- (2-thienyl) -1-propanol.
Stand der TechnikState of the art
(1S)-3-methylamino-1-(2-thienyl)-1 -propanol ist ein wichtiges Zwischenprodukt zur Herstellung von Arzneimitteln, insbesondere von Duloxetin®, einem pharmazeutischen Wirkstoff von EIiLiIIy & Co, USA.(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.
Die Herstellung von (1S)-3-methylamino-1-(2-thienyl)-1 -propanol ist bekannt. Ein gän- giges Herstellverfahren, das in DE 103 48 479A1 detailliert beschrieben ist, betrifft die Umsetzung von Thiophen mit 3-Chlorpropionsäurechlorid in Gegenwart von AICI3, die anschliessende enantioselektive Reduktion der Ketogruppe zu einer Hydroxygruppe und die direkte Aminierung zu (1S)-3-methylamino-1-(2-thienyl)-1 -propanol. Die anschliessende Reinigung von (1S)-3-methylamino-1-(2-thienyl)-1 -propanol erfolgt durch Umkristallisation, bevorzugt aus Methyl-tert.-Butylether.The preparation of (1S) -3-methylamino-1- (2-thienyl) -1-propanol is known. A common preparation process, which is described in detail in DE 103 48 479 A1, relates to the reaction of thiophene with 3-chloropropionic acid chloride in the presence of AICI 3 , the subsequent enantioselective reduction of the keto group to a hydroxy group and the direct amination to (1S) -3 -methylamino-1- (2-thienyl) -1-propanol. The subsequent purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol is carried out by recrystallization, preferably from methyl tert-butyl ether.
In WO 2004/031168 wird ebenfalls die Herstellung von (1S)-3-methylamino-1-(2- thienyl)-1 -propanol beschrieben. Die Aufreinigung von (1S)-3-methylamino-1-(2- thienyl)-1 -propanol erfolgt hier ebenfalls durch Kristallisation aus Methyl-tert.- Butylether.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.
In WO 2004/005307 wird wird ebenfalls die Herstellung von (1S)-3-methylamino-1-(2- thienyl)-1 -propanol beschrieben. Die Aufreinigung von (1S)-3-methylamino-1-(2- thienyl)-1 -propanol erfolgt hier ebenfalls durch Kristallisation aus Methyl-tert- Butylether.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.
Die oben beschriebenen Verfahren zur Reinigung von (1S)-3-methylamino-1-(2- thienyl)-1 -propanol sind von signifikanten Ausbeuteverlusten gekennzeichnet.The above-described methods for purifying (1S) -3-methylamino-1- (2-thienyl) -1-propanol are characterized by significant yield losses.
Aufgabenstellungtask
Es bestand die Aufgabe, ein Reinigungsverfahren für (1S)-3-methylamino-1-(2-thienyl)- 1 -propanol bereitzustellen, dass das Wertprodukt sowohl in hoher chemischer - und Enantiomerenreinheit als auch in einer hohen Ausbeute liefert und das auch im techni- sehen Maßstab unter vertretbaren Kosten durchführbar sein soll. Detaillierte Beschreibung der ErfindungThe 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. Detailed description of the invention
Diese Aufgabe wird gelöst durch ein Verfahren zur Reinigung von (1S)-3-methylamino- 1-(2-thienyl)-1-propanol durch Destillation eines Reaktionsgemisches, das zwischen 25 und 99 Gew.-% (1S)-3-methylamino-1-(2-thienyl)-1-propanol enthält.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.
Der Begriff „Reaktionsgemisch" soll folgende Bedeutung haben: Es kann sich dabei um das nicht aufgereinigte Gemisch aus der Reaktion zur Herstellung von (1S)-3- methylamino-1-(2-thienyl)-1-propanol handeln, also beispielsweise um das Reaktions- gemisch aus Methylamin und (1S)-3-Chlor-1-(2-thienyl)-1-propanol. Es kann sich dabei aber auch -je nach Herstellweg für (1S)-3-methylamino-1-(2-thienyl)-1-propanol - um ein Gemisch aus anderen Reaktionspartnern handeln. Der Begriff „Reaktionsgemisch" umfasst aber auch das aufgereinigte, bzw. teil-gereinigte Reaktionsprόdukt (1S)-3- methylamino-1-(2-thienyl)-1-propanol. Auch eine Lösung von (1S)-3-methylamino-1-(2- thienyl)-1-propanol in einem oder mehreren Lösungsmitteln soll als „Reaktionsgemisch, das ((1S)-3-methylamino-1-(2-thienyl)-1-propanol enthält" verstanden werden.The term "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. Also, 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.
Ein Herstellungsweg für (1S)-3-methylamino-1-(2-thienyl)-1-propanol ist - wie oben bereits erwähnt - ausführlich in DE 103 48479A1 offenbart, auf die hiermit hinsichtlich der Herstellung von (1S)-3-methylamino-1-(2-thienyl)-1-propanol ausdrücklich Bezug genommen wird.A preparation route for (1S) -3-methylamino-1- (2-thienyl) -1-propanol is - as already mentioned above - disclosed in detail in DE 103 48479 A1, which is hereby incorporated with respect to the preparation of (1S) -3-methylamino 1- (2-thienyl) -1-propanol is incorporated by reference.
Aber auch für auf andere Weise hergestelltes (1S)-3-methylamino-1-(2-thienyl)-1- propanol , beispielsweise wie in WO 2004/031168 und in WO 2004/005307 beschrie- ben, auf die hier ebenfalls ausdrücklich Bezug genommen wird, kann das erfindungsgemäße Verfahren mit sehr gutem Erfolg angewendet werden. Denkbar sind auch andere Wege der Darstellung von (1S)-3-methylamino-1-(2-thienyl)-1-propanol , beispielsweise die enzymatische enantioselektive Reduktion der Ketogruppe zur Hydroxy- funktion oder die Umkehrung der in DE 103 48479 beschriebenen Reaktionsfolge, d.h. direkte Aminierung des 3-Chlor-1-(2-thienyl)-1-propanons und anschliessende Reduktion zu (1S)-3-methylamino-1-(2-thienyl)~1-propanol. Für alle diese Herstellverfahren, sowie auch für andere, hier nicht spezifisch genannten Herstellverfahren für (1S)-3- methylamino-1-(2-thienyl)-1-propanol, ist das erfindungsgemäße Verfahren geeignet.But also for (1S) -3-methylamino-1- (2-thienyl) -1-propanol prepared in another way, for example as described in WO 2004/031168 and in WO 2004/005307, to which reference is likewise expressly made here is taken, the inventive method can be applied with great success. Also conceivable are other ways of preparing (1S) -3-methylamino-1- (2-thienyl) -1-propanol, for example the enzymatic enantioselective reduction of the keto group to the hydroxy function or the reversal of the reaction sequence described in DE 103 48479, ie direct amination of 3-chloro-1- (2-thienyl) -1-propanone and subsequent reduction to (1S) -3-methylamino-1- (2-thienyl) -1-propanol. The process according to the invention is suitable for all these preparation processes as well as for other preparation processes for (1S) -3-methylamino-1- (2-thienyl) -1-propanol which are not specifically mentioned here.
Das Reaktionsgemisch enthält den Wertstoff (1S)-3-methylamino-1-(2-thienyl)-1- propanol üblicherweise in einer Menge von 25 bis 99 Gew.-%, bevorzugt von 40 bis 98 Gew.-%, besonders bevorzugt in einer Menge von mehr als 50 Gew.-%.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.
Falls das (1S)-3-methylamino-1-(2-thienyl)-1-propanol in einer geringeren Menge als 25 Gew.-% im Reaktionsgemisch vorliegt, empfiehlt sich üblicherweise ein Konzentrierungsschritt vor der Destillation, beispielsweise das Entfernen von Lösungsmitteln oder das Anreichern von (1S)-3-methylamino-1-(2-thienyl)-1-propanol durch Extraktion. Die Destillation kann in einer Vielzahl von dem Fachmann bekannten Ausgestaltungen durchgeführt werden, wie sie beispielsweise in Handbüchern der Chemischen Technik wie Ulimann oder Winnacker-Küchler ausführlich beschrieben sind.If 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. 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.
Besonders bevorzugte Ausgestaltungen des erfindungsgemäßen Verfahrens sind sogenannte Kurzweg- oder Molekulardestillationen, bei denen mit möglichst kurzen und geradlinig verlaufenden Wegen zwischen Verdampfer- und Kondensatorflächen gearbeitet wird.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.
Besonders gut eignen sich auch kommerziell erhältliche Molekulardestillationsappara- te, wie sie im Fachhandel angeboten werden.Commercially available molecular distillation apparatuses, such as those offered by specialist dealers, are also particularly well suited.
Das erfindungsgemäße Verfahren erlaubt die Reindarstellung von (1S)-3-methylamino- 1-(2-thienyl)-1-propanol in unerwartet hoher chemischer Ausbeute bei gleichzeitiger hoher Reinheit in einem einzigen Arbeitsgang.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.
Experimenteller TeilExperimental part
Beispiel 1:Example 1:
500 g gelbliches Rohmaterial , enthaltend ca. 90 % (1S)-3-methylamino-1-thienyl-1- propanol wurde bei 0,05 mbar und 120 °C Verdampfertemperatur an einem Molekular- destillationsapparat destilliert. Es wurden 420 g ( 93 % Ausbeute) reinweißes Destillat als farbloser Feststoff mit > 99 % Gehalt erhalten.500 g of yellowish crude material containing about 90% (1S) -3-methylamino-1-thienyl-1-propanol was distilled at 0.05 mbar and 120 ° C evaporator temperature on a molecular distillation apparatus. There was obtained 420 g (93% yield) of pure white distillate as a colorless solid> 99% content.
Beispiel 2:Example 2:
500 g dunkelbraunes Rohmaterial , enthaltend ca. 50 % (1S)-3-methylamino-1-thienyl- 1-propanol wurde bei 0,05 mbar und 150 0C Verdampfertemperatur an einem Moleku- lardestillationsapparat destilliert. Es wurden 221 g (88 % Ausbeute) reinweißes Destillat als farbloser Feststoff mit > 99 % Gehalt erhalten.500 g of dark brown crude material, containing about 50% (1S) -3-methylamino-1-thienyl 1-propanol was at 0.05 mbar and 150 0 C evaporator temperature at a molecu- lardestillationsapparat distilled. There were obtained 221 g (88% yield) of pure white distillate as a colorless solid with> 99% content.
Beispiel 3:Example 3:
500 g gelbliches Rohmaterial , enthaltend ca. 98 % (1S)-3-methylamino-1-thienyl-1- propanol wurde bei 0,05 mbar und 100 0C Verdampfertemperatur an einem Molekular- destillationsapparat destilliert. Es wurden 455 g ( 93 % Ausbeute) reinweißes Destillat als farbloser Feststoff mit > 99 % Gehalt erhalten. 500 g of yellowish raw material containing about 98% (1S) -3-methylamino-1-thienyl-1-propanol was at 0.05 mbar and distilled 100 0 C evaporator temperature to a molecular distillation apparatus. There were obtained 455 g (93% yield) of pure white distillate as a colorless solid with> 99% content.

Claims

Patentansprüche claims
1. Verfahren zur Reinigung von (1 S)-3-methylamino-1 -(2-thienyl)-1 -propanol durch Destillation eines Reaktionsgemisches, das zwischen 25 und 99 Gew.-% (1S)-3- methylamino-1-(2-thienyl)-1 -propanol enthält.A process for the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol by the distillation of a reaction mixture containing between 25 and 99% by weight of (1S) -3-methylamino-1 Contains (2-thienyl) -1-propanol.
2. Verfahren nach Anspruch 1 , dadurch gekennzeichnet, dass die Destillation in einem Druckbereich von 0,0001 bis 1 mbar durchgeführt wird.2. The method according to claim 1, characterized in that the distillation is carried out in a pressure range of 0.0001 to 1 mbar.
3. Verfahren nach Anspruch.2, dadurch gekennzeichnet, dass die Destillation als Molekulardestillation durchgeführt wird.3. The method according to claim 2, characterized in that the distillation is carried out as a molecular distillation.
4. Verfahren nach Anspruch 1-3, dadurch gekennzeichnet, dass die Destillation bei einer Temperatur von 50 bis 25O0C durchgeführt wird. 4. The method according to claim 1-3, characterized in that the distillation at a temperature of 50 to 25O 0 C is performed.
EP05820701A 2005-01-05 2005-12-31 Method for purifying (1s)-3-methylamino-1-(2-thienyl)-1-propanol Withdrawn EP1836185A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005000867A DE102005000867A1 (en) 2005-01-05 2005-01-05 Process for the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol
PCT/EP2005/014161 WO2006072465A1 (en) 2005-01-05 2005-12-31 Method for purifying (1s)-3-methylamino-1-(2-thienyl)-1-propanol

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EP1836185A1 true EP1836185A1 (en) 2007-09-26

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

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CN107417663B (en) * 2017-09-25 2019-05-28 台州职业技术学院 A kind of preparation method of high-purity (S) -3- methylamino -1- (thiophene -2- base) propyl alcohol

Citations (1)

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Publication number Priority date Publication date Assignee Title
WO2004031168A2 (en) * 2002-10-07 2004-04-15 Lonza Ag Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives

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Publication number Priority date Publication date Assignee Title
WO2004005307A1 (en) * 2002-07-09 2004-01-15 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 (en) * 2002-10-07 2004-04-15 Lonza Ag Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives

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DE102005000867A1 (en) 2006-07-13
CN101098863B (en) 2010-09-15
CA2590660A1 (en) 2006-07-13
US20080108835A1 (en) 2008-05-08
CN101098863A (en) 2008-01-02
WO2006072465A1 (en) 2006-07-13
JP2008526703A (en) 2008-07-24

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