WO2001016089A1 - A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride - Google Patents

A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride Download PDF

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Publication number
WO2001016089A1
WO2001016089A1 PCT/IB2000/001182 IB0001182W WO0116089A1 WO 2001016089 A1 WO2001016089 A1 WO 2001016089A1 IB 0001182 W IB0001182 W IB 0001182W WO 0116089 A1 WO0116089 A1 WO 0116089A1
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WO
WIPO (PCT)
Prior art keywords
formula
cis
hydrochloride
dichlorophenyl
compound
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.)
Ceased
Application number
PCT/IB2000/001182
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English (en)
French (fr)
Inventor
Sharad Kumar Vyas
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.)
Individual
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to AU65875/00A priority Critical patent/AU6587500A/en
Publication of WO2001016089A1 publication Critical patent/WO2001016089A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen

Definitions

  • This invention relates to a process for the preparation of N-methyl-4-
  • sertraline hydrochloride which is cis-(l S,4S)-N-methyl-4-(3 ,4-
  • serotonin resides in the cis-1 S,4S isomer i.e. cis-(l S, 4S)-N-methyl-4-
  • hydrochloride (I) commonly known as sertraline hydrochloride.
  • hydrochloride (II) are known in the literature.
  • the inline was hydrogenated using 10% Pd/C as catalyst to give the
  • a metal hydride reagent e.g. sodium
  • titanium tetrachloride is crucial, as the reagent is moisture sensitive and
  • the first object of the invention is to produce sertraline hydrochloride
  • Another object of the present invention is to produce cis-N-methyl-4-
  • Yet another object of the present invention is to produce the said
  • the present invention provides a process for preparation
  • naphthalenearnine hydrochloride i.e. sertraline hydrochloride of the
  • metal catalyst such as Raney Nickel
  • the invention also provides for preparation of intermediate cis-N-
  • hydrochloride of formula - VI which comprises the process steps (a), (b)
  • Solvent for the reaction is protic polar in the nature.
  • Protic polar solvent is protic polar solvent
  • lower alcohol such as C 1 -C 3 alcohols may be used.
  • C 1 -C 3 alcohols may be used.
  • the temperature as one of the preferred
  • parameters may be varied over the range of room temperature to 100°C.
  • Preferred solvent is methanol.
  • Preferred hydrogen pressure is 450-500 psi
  • isomer is carried out by separating all cis-isomers from the said isomeric
  • naphthalenone (15.0 gm) is taken, followed by addition of 250 ml.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/IB2000/001182 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride Ceased WO2001016089A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU65875/00A AU6587500A (en) 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahyd ro-1-naphthaleneamine hydrochloride

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN748CA1999 IN185109B (cs) 1999-09-01 1999-09-01
IN748/CAL/99 1999-09-01

Publications (1)

Publication Number Publication Date
WO2001016089A1 true WO2001016089A1 (en) 2001-03-08

Family

ID=11084493

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2000/001182 Ceased WO2001016089A1 (en) 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride

Country Status (4)

Country Link
AR (1) AR025461A1 (cs)
AU (1) AU6587500A (cs)
IN (1) IN185109B (cs)
WO (1) WO2001016089A1 (cs)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002096860A1 (en) * 2001-05-31 2002-12-05 Orion Corporation Fermion Process for preparing sertraline intermediates
US6723878B2 (en) 2001-06-15 2004-04-20 Orion Corporation Fermion Method for preparing sertraline
US6809221B2 (en) 2000-03-14 2004-10-26 Teva Pharmaceutical Industries Ltd. Process for preparing (+)-cis-sertraline
US6897340B2 (en) 2002-04-29 2005-05-24 Teva Pharmaceutical Industries Ltd. Processes for preparation of polymorphic form II of sertraline hydrochloride
WO2006091732A1 (en) * 2005-02-23 2006-08-31 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
WO2006129324A2 (en) 2005-06-03 2006-12-07 Hetero Drugs Limited A highly stereoselective synthesis of sertraline
US7262327B2 (en) 2003-09-05 2007-08-28 Teva Pharmaceutical Industries Ltd. Recycling process for preparing sertraline
US7276629B2 (en) 2003-04-14 2007-10-02 Teva Pharmaceutical Industries Ltd. Hydrogenation of imine intermediates of sertraline with catalysts
US7345201B2 (en) 2005-02-23 2008-03-18 Teva Pharmaceutical Industries, Ltd. Processes for preparing sertraline
WO2007119247A3 (en) * 2006-04-17 2009-05-14 Unichem Lab Ltd Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030081A1 (en) * 1979-11-01 1981-06-10 Pfizer Inc. Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof
WO1999036394A1 (en) * 1998-01-16 1999-07-22 Pfizer Products Inc. Novel process for preparing a ketimine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030081A1 (en) * 1979-11-01 1981-06-10 Pfizer Inc. Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof
WO1999036394A1 (en) * 1998-01-16 1999-07-22 Pfizer Products Inc. Novel process for preparing a ketimine

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6809221B2 (en) 2000-03-14 2004-10-26 Teva Pharmaceutical Industries Ltd. Process for preparing (+)-cis-sertraline
WO2002096860A1 (en) * 2001-05-31 2002-12-05 Orion Corporation Fermion Process for preparing sertraline intermediates
US6723878B2 (en) 2001-06-15 2004-04-20 Orion Corporation Fermion Method for preparing sertraline
US6897340B2 (en) 2002-04-29 2005-05-24 Teva Pharmaceutical Industries Ltd. Processes for preparation of polymorphic form II of sertraline hydrochloride
US7276629B2 (en) 2003-04-14 2007-10-02 Teva Pharmaceutical Industries Ltd. Hydrogenation of imine intermediates of sertraline with catalysts
US7262327B2 (en) 2003-09-05 2007-08-28 Teva Pharmaceutical Industries Ltd. Recycling process for preparing sertraline
WO2006091732A1 (en) * 2005-02-23 2006-08-31 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
US7345201B2 (en) 2005-02-23 2008-03-18 Teva Pharmaceutical Industries, Ltd. Processes for preparing sertraline
US7518018B2 (en) 2005-02-23 2009-04-14 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
WO2006129324A2 (en) 2005-06-03 2006-12-07 Hetero Drugs Limited A highly stereoselective synthesis of sertraline
WO2007119247A3 (en) * 2006-04-17 2009-05-14 Unichem Lab Ltd Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)

Also Published As

Publication number Publication date
IN185109B (cs) 2000-11-18
AR025461A1 (es) 2002-11-27
AU6587500A (en) 2001-03-26

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