DK2867195T3 - Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1- propanal med chloracetone - Google Patents

Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1- propanal med chloracetone Download PDF

Info

Publication number
DK2867195T3
DK2867195T3 DK12784615.2T DK12784615T DK2867195T3 DK 2867195 T3 DK2867195 T3 DK 2867195T3 DK 12784615 T DK12784615 T DK 12784615T DK 2867195 T3 DK2867195 T3 DK 2867195T3
Authority
DK
Denmark
Prior art keywords
reaction
compound
formula
acid
reac
Prior art date
Application number
DK12784615.2T
Other languages
English (en)
Inventor
Doerwald Florencio Zaragoza
Anna Kulesza
Stephan Elzner
Robert Bujok
Zbigniew Wrobel
Krzysztof Wojciechowski
Original Assignee
Lonza Ag
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=47558545&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DK2867195(T3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from PCT/EP2012/070879 external-priority patent/WO2012172122A2/en
Application filed by Lonza Ag filed Critical Lonza Ag
Application granted granted Critical
Publication of DK2867195T3 publication Critical patent/DK2867195T3/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/02—Monocyclic aromatic halogenated hydrocarbons
    • C07C25/125—Halogenated xylenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/105—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings
    • C07C49/11—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
    • C07D301/26—Y being hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Fats And Perfumes (AREA)

Claims (6)

  1. FREMGANGSMÅDE TIL FREMSTILLING AF 2-(2,3-DIMETHYLPHENYL)-1-PROPANAL MED CHLORACETONE
    1. Fremgangsmåde til fremstilling af forbindelse med formlen (XXI);
    fremgangsmåden omfatter to trin, de to trin er et trin (Q1) og et trin (Q2); trin (Q1) omfatter en reaktion (Q1-reag); reaktion (Q1-reac) er en reaktion af forbindelse med formlen (XXV) med et reagens (Q1-reag);
    R1 er Br, Cl eller I; reagent (Q1-reag) er udvalgt fra gruppen bestående af lithium, magnesium, aluminium, zink, calcium, propylmagnesiumchlorid, propylmagnesiumbromid, butyllithium og blandinger deraf; trin (Q2) omfatter en reaktion (Q2-reac); reaktion (Q2-reac) er en reaktion af reaktionsproduktet af reaktion (Q1-reac) med chloracetone; reaktionsproduktet af reaktion (Q2-reac) er forbindelse med formlen (XXII);
    der omdannes til forbindelse med formlen (XXI).
  2. 2. Fremgangsmåde ifølge krav 1, hvor R1 er Br.
  3. 3. Fremgangsmåde ifølge krav 1 eller 2, hvor reagent (Q1-reag) er udvalgt fra gruppen bestående af lithium, magnesium, aluminium, isopropylmagnesiumchlorid, isopropylmagnesiumbromid, n-butyllithium, sec-butyllithium, tert-butyllithium og blandinger deraf.
  4. 4. Fremgangsmåde ifølge et eller flere af kravene 1 til 3, hvor reaktion (Q1 -reac) sker i nærvær af en katalysator (Q1-cat); katalysator (Q1-cat) er udvalgt fra gruppen bestående af iod, 1,2-dibromethan, TiCU, AlCb, PbCb, B1CI3, LiCI og blandinger deraf.
  5. 5. Fremgangsmåde ifølge et eller flere af kravene 1 til 4, hvorforbindelse med formlen (XXI) fremstilles i et trin (N); trin (N) udføres efter trin (Q2); trin (N) omfatter en reaktion (N-reac); reaktion (N-reac) er en reaktion af forbindelse med formlen (XXII) med en katalysator (N-cat);
    katalysator (N-cat) er udvalgt fra gruppen bestående af eddikesyre, myresyre, trifluoreddikesyre, methansulfonsyre, benzensulfonsyre, p- toluensulfonsyre,camphersulfonsyre, HCI, HBr, H2SO4, HNO3, H3PO4, HCIO4, BCb, BBr3, BF3OEt2, BF3SMe2, BF3THF, MgCI2, MgBr2, Mgl2, AICIs, AI(0-Ci-4-alkyl)3, SnCL, TiCU, Ti(0-Ci-4-alkyl)4, ZrCU, B12O3, BiCb, ZnCb, PbCl2, FeCb, ScCI3, NiCI2, Yb(OTf)3, Yb(CI)3, GaCI3, AIBr3, Ce(OTf)3, LiCI, Cu(BF4)2, Cu(OTf)2, NiBr2(PPh3)2, NiBr2, N1CI2, Pd(OAc)2, PdCb, PtCb, InCb, surt, uorganisk faststof, sur ionbytterharpiks, carbon-behandlet med uorganisk syre og blandinger deraf; forbindelse med formlen (XXII) er reaktionsproduktet af reaktion (Q2-reac).
  6. 6. Fremgangsmåde ifølge krav 5, hvor katalysator (N-cat) er udvalgt fra gruppen bestående af eddikesyre, myresyre, trifluoreddikesyre, methansulfonsyre, p-toluensulfonsyre, HCI, HBr, H2SO4, H3PO4, BCb, BF3<DEt2, MgCb, MgBr2, AlCb, ZnCl2, Cu(BF4)2, aluminiumsilicat, sur ionbytterharpiks, carbon-behandlet med HCI, H2SO4 eller HNO3 og blandinger deraf.
DK12784615.2T 2012-06-28 2012-11-15 Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1- propanal med chloracetone DK2867195T3 (da)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US201261665528P 2012-06-28 2012-06-28
EP12174104 2012-06-28
EP12189239 2012-10-19
PCT/EP2012/070879 WO2012172122A2 (en) 2012-06-28 2012-10-22 Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal
EP12192627 2012-11-14
PCT/EP2012/072799 WO2013011158A2 (en) 2012-06-28 2012-11-15 Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal with chloroacetone

Publications (1)

Publication Number Publication Date
DK2867195T3 true DK2867195T3 (da) 2016-04-04

Family

ID=47558545

Family Applications (1)

Application Number Title Priority Date Filing Date
DK12784615.2T DK2867195T3 (da) 2012-06-28 2012-11-15 Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1- propanal med chloracetone

Country Status (22)

Country Link
US (1) US9126914B1 (da)
EP (1) EP2867195B1 (da)
JP (1) JP5779298B2 (da)
KR (1) KR101537203B1 (da)
CN (1) CN104220408B (da)
AU (1) AU2012285678B2 (da)
BR (1) BR112014022268A8 (da)
CA (1) CA2866441C (da)
CL (1) CL2014002906A1 (da)
CY (1) CY1117491T1 (da)
DK (1) DK2867195T3 (da)
EA (1) EA024425B1 (da)
ES (1) ES2565065T3 (da)
HK (1) HK1200810A1 (da)
HR (1) HRP20160250T1 (da)
HU (1) HUE027383T2 (da)
IN (1) IN2014DN08121A (da)
MY (1) MY165118A (da)
PL (1) PL2867195T3 (da)
SG (1) SG11201405608QA (da)
TW (1) TWI535692B (da)
WO (1) WO2013011158A2 (da)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG11201405606RA (en) 2012-05-08 2014-11-27 Lonza Ag Method for preparation of medetomidine
KR101537204B1 (ko) 2012-05-08 2015-07-22 론자 아게 (론자 엘티디.) 2-(2,3-디메틸페닐)-1-프로파날의 제조 방법
PL2867195T3 (pl) * 2012-06-28 2016-06-30 Lonza Ag Sposób wytwarzania 2-(2,3-dimetylofenylo)-1-propanalu przy pomocy chloroacetonu
CN104245678B (zh) * 2012-06-28 2016-02-24 隆萨有限公司 用氯丙酮制备美托咪定的方法
US11221599B2 (en) 2014-11-28 2022-01-11 Signify Holding B.V. Systems and methods for managing environmental conditions
CN106518812A (zh) * 2016-10-25 2017-03-22 湖南大学 一种美托咪定及其中间体的制备方法
CN106749030B (zh) * 2016-12-15 2019-02-12 禚修洁 一种用于icu镇静镇痛的盐酸右美托咪定的制备方法
KR102148289B1 (ko) * 2018-07-04 2020-08-26 에스에프씨주식회사 고효율의 유기 발광 소자
KR102495135B1 (ko) * 2019-04-03 2023-02-02 주식회사 엘지에너지솔루션 리튬 이차 전지용 전해질 및 이를 포함하는 리튬 이차 전지
US10889536B1 (en) 2019-09-04 2021-01-12 Eastman Chemical Company Enol ethers
US10815179B1 (en) 2019-09-04 2020-10-27 Eastman Chemical Company Aromatic dicarbinols
US10858304B1 (en) 2019-09-04 2020-12-08 Eastman Chemical Company Aromatic enol ethers
US10544076B1 (en) 2019-09-04 2020-01-28 Eastman Chemical Company Method of making a dialdeyhde
US10550057B1 (en) * 2019-09-04 2020-02-04 Eastman Chemical Company Method of making a dialdeyhde
US10865172B1 (en) 2019-09-04 2020-12-15 Eastman Chemical Company Aromatic enol ethers
US11518899B2 (en) 2019-09-04 2022-12-06 Eastman Chemical Company Aromatic enol ether paint additives
US11312873B2 (en) 2019-09-04 2022-04-26 Eastman Chemical Company Aromatic enol ether paint additives
US10865171B1 (en) 2019-09-04 2020-12-15 Eastman Chemical Company Process to make aromatic enol ethers and olefin isomers of aromatic enol ethers

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE790604A (fr) 1971-10-28 1973-04-26 Sandoz Sa Nouveaux aminoalcanols, leur preparation et leur application comme medicaments
JPS51100042A (en) * 1975-02-26 1976-09-03 Kanebo Ltd 22 * 44 isobuchirufueniru * puropionsanno seizoho
JPS51100041A (en) * 1975-02-26 1976-09-03 Kanebo Ltd 22 * 44 isobuchirufueniru * puropionsanno seizoho
GB2092569B (en) 1981-02-05 1984-09-19 Farmos Oy Substituted imidazole derivatives and their preparation and use
GB2101114B (en) 1981-07-10 1985-05-22 Farmos Group Ltd Substituted imidazole derivatives and their preparation and use
ATE78722T1 (de) * 1984-02-24 1992-08-15 Sagami Chem Res Methode zum isomerisieren eines glycidats.
JPS62103037A (ja) * 1985-10-29 1987-05-13 Hamari Yakuhin Kogyo Kk ２−（４−イソブチルフエニル）−プロピオンアルデヒドの製造法
DE19714042A1 (de) 1997-04-05 1998-10-08 Henkel Kgaa Verfahren zur Herstellung aromatischer Aldehyde
SE513474C2 (sv) 1999-01-25 2000-09-18 Hans Elwing Instutionen Foer C Metod för att förhindra kräftdjurs, särskilt havstulpaners, etablering på fasta ytor med hjälp av en substans som stör nervsignaler, varvid substansen är medetomidin, dvs (+)-4-/1- (2,3-dimetylfenyl)-etyl/-IH-imidazol
EP1918282A1 (en) * 2006-11-06 2008-05-07 "Joint Stock Company Grindeks" Method for preparing medetomidine and its salts
GB2453982B (en) 2007-10-24 2009-09-16 Norbrook Lab Ltd Chemical process for the preparation of Medetomidine
US7902247B2 (en) 2008-01-09 2011-03-08 Allergan, Inc. Substituted-aryl-2-phenylethyl-1H-imidazole compounds as subtype selective modulators of alpha 2B and/or alpha 2C adrenergic receptors
WO2011070069A1 (en) 2009-12-09 2011-06-16 I-Tech Ab Process for preparation of medetomidine
KR101537204B1 (ko) * 2012-05-08 2015-07-22 론자 아게 (론자 엘티디.) 2-(2,3-디메틸페닐)-1-프로파날의 제조 방법
SG11201405606RA (en) * 2012-05-08 2014-11-27 Lonza Ag Method for preparation of medetomidine
WO2012172119A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd Method for the preparation of medetomidine
WO2012172120A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume
CN104245678B (zh) * 2012-06-28 2016-02-24 隆萨有限公司 用氯丙酮制备美托咪定的方法
WO2012172121A1 (en) * 2012-06-28 2012-12-20 Lonza Ltd Method for the preparation of medetomidine with chloroacetone
PL2867195T3 (pl) * 2012-06-28 2016-06-30 Lonza Ag Sposób wytwarzania 2-(2,3-dimetylofenylo)-1-propanalu przy pomocy chloroacetonu
WO2012172122A2 (en) * 2012-06-28 2012-12-20 Lonza Ltd Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal

Also Published As

Publication number Publication date
KR101537203B1 (ko) 2015-07-22
CL2014002906A1 (es) 2014-12-12
EP2867195A2 (en) 2015-05-06
EA024425B1 (ru) 2016-09-30
HUE027383T2 (en) 2016-10-28
TW201402533A (zh) 2014-01-16
WO2013011158A2 (en) 2013-01-24
WO2013011158A3 (en) 2013-05-10
NZ700643A (en) 2016-03-31
US20150239816A1 (en) 2015-08-27
BR112014022268A8 (pt) 2019-05-28
BR112014022268A2 (da) 2017-06-20
JP2015517475A (ja) 2015-06-22
JP5779298B2 (ja) 2015-09-16
CA2866441A1 (en) 2013-01-24
CN104220408B (zh) 2016-01-20
AU2012285678A1 (en) 2014-09-25
ES2565065T3 (es) 2016-03-31
CY1117491T1 (el) 2017-04-26
HK1200810A1 (zh) 2015-08-14
EA201400938A1 (ru) 2015-01-30
SG11201405608QA (en) 2014-11-27
CA2866441C (en) 2017-01-17
AU2012285678B2 (en) 2016-02-25
HRP20160250T1 (hr) 2016-04-08
US9126914B1 (en) 2015-09-08
IN2014DN08121A (da) 2015-05-01
MY165118A (en) 2018-02-28
PL2867195T3 (pl) 2016-06-30
EP2867195B1 (en) 2015-12-30
TWI535692B (zh) 2016-06-01
CN104220408A (zh) 2014-12-17
KR20140131599A (ko) 2014-11-13

Similar Documents

Publication Publication Date Title
DK2867195T3 (da) Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1- propanal med chloracetone
DK2867211T3 (da) Fremgangsmåde til fremstilling af medetomidin med chloracetone
DK2847173T3 (da) Fremgangsmåde til fremstilling af medetomidin
WO2012172122A2 (en) Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal
WO2012172120A2 (en) 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume
US9126915B2 (en) Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal
WO2012172119A2 (en) Method for the preparation of medetomidine
AU2012285676A1 (en) Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal
WO2012172121A1 (en) Method for the preparation of medetomidine with chloroacetone
NZ700643B2 (en) Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal with chloroacetone
NZ700640B2 (en) Method for preparation of medetomidine
NZ700642B2 (en) Method for preparation of medetomidine with chloroacetone