WO2011092719A3 - Process for preparing 1 -phenyl-3 -dimethylaminopropane derivatives - Google Patents

Process for preparing 1 -phenyl-3 -dimethylaminopropane derivatives Download PDF

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Publication number
WO2011092719A3
WO2011092719A3 PCT/IN2011/000060 IN2011000060W WO2011092719A3 WO 2011092719 A3 WO2011092719 A3 WO 2011092719A3 IN 2011000060 W IN2011000060 W IN 2011000060W WO 2011092719 A3 WO2011092719 A3 WO 2011092719A3
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WO
WIPO (PCT)
Prior art keywords
phenyl
preparing
aralkyl
heteroaryl
aryl
Prior art date
Application number
PCT/IN2011/000060
Other languages
French (fr)
Other versions
WO2011092719A2 (en
Inventor
Shekhar Bhaskar Bhirud
Perminder Singh Johar
Ekta Sharma
Danish Jamshad
Ramkaran Prajapaty
Original Assignee
Ind-Swift Laboratories Limited
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 Ind-Swift Laboratories Limited filed Critical Ind-Swift Laboratories Limited
Publication of WO2011092719A2 publication Critical patent/WO2011092719A2/en
Publication of WO2011092719A3 publication Critical patent/WO2011092719A3/en

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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
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Process for preparing 1-phenyl-3-dimethylaminopropane derivatives of formula (I), and pharmaceutically acceptable salts thereof from intermediate of formula (II) are provided, wherein R1 can be selected from -OR2, halo, -CH2OR2, -SR2, SOR2, SO2R2, -SO3H, -NO2, -NR2R2', - CONR2R2 ', and the like; R ' can be selected from hydrogen, alkyl, aryl, aralkyl, alkaryl, heteroaryl, and the like; or R2 and R2 ' can be same or different and can be selected from hydrogen, alkyl, aryl, aralkyl, heteroaryl,-OR3, - COR3, -PO3(R3R1) wherein R1 and R4 can be same or different and can be selected from alkyl, aryl, aralkyl, heteroaryl and the like.
PCT/IN2011/000060 2010-02-01 2011-01-28 Process for the preparation of l-phenyl-3-dimethylaminopropane derivatives WO2011092719A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN221/DEL/2010 2010-02-01
IN221DE2010 2010-02-01
IN1579/DEL/2010 2010-07-06
IN1579DE2010 2010-07-06

Publications (2)

Publication Number Publication Date
WO2011092719A2 WO2011092719A2 (en) 2011-08-04
WO2011092719A3 true WO2011092719A3 (en) 2011-09-22

Family

ID=44319929

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2011/000060 WO2011092719A2 (en) 2010-02-01 2011-01-28 Process for the preparation of l-phenyl-3-dimethylaminopropane derivatives

Country Status (1)

Country Link
WO (1) WO2011092719A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102477016B (en) * 2010-11-26 2014-12-17 中国医学科学院药物研究所 Synthesis and application of intermediate of tapentadol
CN102617501A (en) * 2011-01-31 2012-08-01 中国科学院上海药物研究所 Substituted valeramide compound, preparation method and application thereof
US8853393B2 (en) * 2011-07-29 2014-10-07 Anhui New Star Pharmaceutical Development Co., Ltd. Intermediate for preparing tapentadol or analogues thereof
EP2674414A1 (en) 2012-06-15 2013-12-18 Siegfried AG Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds
CN102936205B (en) * 2012-11-12 2014-06-18 合肥市新星医药化工有限公司 Synthesis method of tapentadol
WO2015075678A1 (en) 2013-11-21 2015-05-28 Unimark Remedies Ltd. A novel process for the preparation of 1-phenyl-3-aminopropane derivatives
CN104725287A (en) * 2013-12-20 2015-06-24 北京蓝贝望生物医药科技股份有限公司 Preparation method and application of para-toluenesulfonate
CN103787898B (en) * 2014-01-17 2016-05-25 暨明医药科技（苏州）有限公司 A kind of synthetic method of tapentadol hydrochloride
JP6502397B2 (en) * 2014-07-10 2019-04-17 スペックジーエックス エルエルシー Method for producing substituted phenyl alkane
US9914695B2 (en) 2015-07-10 2018-03-13 Mallinckrodt Llc Two-step process for preparing 3-substituted phenylalkylamines
CN111056961A (en) * 2019-11-13 2020-04-24 李晓强 Preparation method of 3- ((1S,2S) -3-dimethylamino-1-ethyl-2-methylpropyl) phenol hydrochloride

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248737B1 (en) * 1994-07-23 2001-06-19 Gruenenthal Gmbh 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
WO2004108658A1 (en) * 2003-06-06 2004-12-16 Grünenthal GmbH Method for the production of substituted 3-aryl-butyl amine compounds
WO2008012283A1 (en) * 2006-07-24 2008-01-31 Janssen Pharmaceutica Nv Preparation of (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentanamine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248737B1 (en) * 1994-07-23 2001-06-19 Gruenenthal Gmbh 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
WO2004108658A1 (en) * 2003-06-06 2004-12-16 Grünenthal GmbH Method for the production of substituted 3-aryl-butyl amine compounds
WO2008012283A1 (en) * 2006-07-24 2008-01-31 Janssen Pharmaceutica Nv Preparation of (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentanamine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ABSTRACT & ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICAE, vol. 40, no. 3, 1964, pages 295 - 307 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE; 1965, "Preparation of 1-aryl-isobenzopyrylium salts", accession no. STN Database accession no. 1616-70-2 *

Also Published As

Publication number Publication date
WO2011092719A2 (en) 2011-08-04

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