DK2668151T3 - Fremgangsmåde til fremstilling af 2,2-difluorethylamin med udgangspunkt i 2,2-difluor-1-chlorethan - Google Patents

Fremgangsmåde til fremstilling af 2,2-difluorethylamin med udgangspunkt i 2,2-difluor-1-chlorethan Download PDF

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Publication number
DK2668151T3
DK2668151T3 DK12700495.0T DK12700495T DK2668151T3 DK 2668151 T3 DK2668151 T3 DK 2668151T3 DK 12700495 T DK12700495 T DK 12700495T DK 2668151 T3 DK2668151 T3 DK 2668151T3
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DK
Denmark
Prior art keywords
formula
bromide
process according
acid
approximately
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DK12700495.0T
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English (en)
Inventor
Norbert Lui
Jens-Dietmar Heinrich
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Bayer Ip Gmbh
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Publication of DK2668151T3 publication Critical patent/DK2668151T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (10)

1. Fremgangsmåde til fremstilling af 2,2-difluorethylamin, som omfatter følgende trin: trin (i): omsætning af 2,2-difluor-1-chlorethan med formel (I) CHF2-CH2CI (I), med en imid med formel (II)
(II) i nærvær af en base til en forbindelse med formel (III)
(III) hvor R1 og R2 i forbindelserne med formel (II) og (III) hver især uafhængigt af hinanden står for hydrogen eller C1-C6-alkyl, eller R1 og R2 sammen med det carbonatom, som de er bundet til, danner en seksleddet, aromatisk ring, som i givet fald er substitueret; og hvori det molære forhold mellem basen og den anvendte imid med formel (II) ligger i området fra 0,8 til 5, trin (ii) : fraspaltning af 2,2-difluorethylamin ved hjælp af reaktion af forbindelsen med formel (III) med syre, base eller hydrazin.
2. Fremgangsmåde ifølge krav 1, idet forbindelsen med formel (II) foreligger som salt.
3. Fremgangsmåde ifølge krav 1 eller 2, idet forbindelsen med formel (II) er succinimid eller phthalimid.
4. Fremgangsmåde ifølge et af kravene 1 til 3, idet basen i trin (i) er udvalgt blandt tertiære aminer, substituerede eller usubstituerede pyridiner og substituerede eller usubstituerede quinoliner, triethylamin, trimethylamin, diisopropylethylamin, tri-n-propylamin, tri-n-butylamin, tri- n-hexylamin, tricyclohexylamin, N-methyl-cyclohexylamin, N-methylpyrrolidin, N-methylpiperidin, N-ethylpiperidin, N,N-dimethylanilin, N-methylmorpholin, pyridin, 2-, 3-, 4-picolin, 2-methyl-5-ethyl-pyridin, 2,6-lutidin, 2,4,6-collidin, 4-dimethylaminopyridin, quinolin, quinaldin, Ν,Ν,Ν,Ν- tetramethylenethyldiamin, N, N-dimethyl-1,4-diazacyclohexan, N,N-Di-ethyl-1,4-diazacyclohexan, 1,8-bis-(dimethyl- amino) naphthalin, diazabicyclooctan (DABCO), diazabicyclononan (DBN), diazabicycloundecan (DBU), butylimidazol, methylimidazol, natriumhydroxid, kaliumhydroxid, lithiumhydroxid, calciumhydroxid, natriumcarbonat, kaliumcarbonat, natriumhydrogencarbonat, kaliumhydrogencarbonat og natriumacetat.
5. Fremgangsmåde ifølge et af kravene 1 til 3, idet basen i trin (i) er kaliumcarbonat eller natriumcarbonat.
6. Fremgangsmåde ifølge et af kravene 1 til 5, idet der i trin (i) endvidere findes en katalysator, idet katalysatoren er udvalgt blandt alkalibromider og -jodider, ammoniumbromid, ammoniumjodid, tetraalkylammoniumbromider og -jodider, tetraalkyl- eller tetraarylphosphoniumhalogenider, tetrahis(dimethylamino)phosphoniumbromid, tetrahis(diethylamino)phosphoniumbromid, tetrakis(dipropylamino)phosphoniumchlorid eller -bromid og bis(dimethylamino)[(1,3-dimethylimidazolidin-2-yliden)amino] methyliumbromid.
7. Fremgangsmåde ifølge krav 6, idet katalysatoren er natriumbromid, kaliumbromid, natriumjodid, kaliumjodid eller tetrabutylammoniumbromid.
8. Fremgangsmåde ifølge et af kravene 1 til 7, idet der i trin (ii) anvendes uorganiske syrer.
9. Fremgangsmåde ifølge krav 8, idet den uorganiske syre er saltsyre, hydrogenbromid, svovlsyre eller phosphorsyre.
10. Fremgangsmåde ifølge et af kravene 1 til 9, idet det molære forhold mellem syre og imiden med formel (III) ligger i området fra 0,8 til 100.
DK12700495.0T 2011-01-24 2012-01-20 Fremgangsmåde til fremstilling af 2,2-difluorethylamin med udgangspunkt i 2,2-difluor-1-chlorethan DK2668151T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161435497P 2011-01-24 2011-01-24
EP11151873 2011-01-24
PCT/EP2012/050834 WO2012101044A1 (de) 2011-01-24 2012-01-20 Verfahren zur herstellung von 2,2-difluorethylamin ausgehend von 2,2-difluor-1-chlorethan

Publications (1)

Publication Number Publication Date
DK2668151T3 true DK2668151T3 (da) 2017-01-30

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DK12700495.0T DK2668151T3 (da) 2011-01-24 2012-01-20 Fremgangsmåde til fremstilling af 2,2-difluorethylamin med udgangspunkt i 2,2-difluor-1-chlorethan

Country Status (12)

Country Link
US (1) US8580973B2 (da)
EP (1) EP2668151B1 (da)
JP (1) JP5952305B2 (da)
KR (1) KR20140005994A (da)
CN (1) CN103443067B (da)
BR (1) BR112013018974A2 (da)
DK (1) DK2668151T3 (da)
ES (1) ES2613709T3 (da)
IL (1) IL227592A (da)
MX (1) MX2013008595A (da)
TW (1) TWI518055B (da)
WO (1) WO2012101044A1 (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6182507B2 (ja) * 2014-05-30 2017-08-16 日本曹達株式会社 ２，３−ジハロゲノアニリンの製造方法
CN104030928B (zh) * 2014-06-04 2016-01-20 湖北海之杰化工有限公司 2,2-二氟乙胺的制备方法
CN112645822B (zh) * 2020-12-09 2022-06-07 苏州当量生物医药有限公司 2-氟乙胺盐酸盐的制备方法
MX2023009607A (es) 2021-02-17 2024-01-08 Bayer Ag Un proceso para la preparacion de polifluoroalquilaminas de polifluoroalquilalcoholes.

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4030994A (en) * 1971-06-18 1977-06-21 Merck & Co., Inc. Substitutive fluorination of organic compounds
HU223057B1 (hu) * 1997-12-15 2004-03-01 Richter Gedeon Vegyészeti Gyár Rt. Eljárás helyettesített allilamin-származék és sói előállítására
JP2001131177A (ja) * 1999-11-08 2001-05-15 Ohara Yakuhin Kogyo Kk ジベンズ［ｃ，ｆ］イミダゾ［１，５−ａ］アゼピンの製造方法及びその製造中間体
JP2002308851A (ja) * 2001-04-13 2002-10-23 Daito Kk ６−アミノメチル−６，１１−ジヒドロ−５Ｈ−ジベンゾ［ｂ，ｅ］アゼピンの製造方法
DE102006015467A1 (de) * 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
DE102006033572A1 (de) * 2006-07-20 2008-01-24 Bayer Cropscience Ag N'-Cyano-N-halogenalkyl-imidamid Derivate
WO2008134327A1 (en) * 2007-04-26 2008-11-06 Dow Global Technologies Inc. Method of producing amino dialkoxy aldehydes via hydroformylation
EP2039684A1 (de) 2007-09-18 2009-03-25 Bayer CropScience AG Verfahren zur Herstellung von 2,2-Difluorethylamin-Derivaten durch Imin-Hydrierung
KR101682259B1 (ko) * 2008-12-22 2016-12-05 포라 가세이 고교 가부시키가이샤 멜라닌 생산 억제제
FR2941454B1 (fr) * 2009-01-29 2011-04-01 Pf Medicament Proced de synthese du (1s,2r)-milnacipran
WO2010123999A2 (en) * 2009-04-21 2010-10-28 Auspex Pharmaceuticals, Inc. 1-methylpyrazole modulators of substance p, calcitonin gene-related peptide, adrenergic receptor, and/or 5-ht receptor

Also Published As

Publication number Publication date
KR20140005994A (ko) 2014-01-15
US8580973B2 (en) 2013-11-12
EP2668151A1 (de) 2013-12-04
BR112013018974A2 (pt) 2017-03-21
MX2013008595A (es) 2013-08-14
EP2668151B1 (de) 2016-11-16
WO2012101044A1 (de) 2012-08-02
TWI518055B (zh) 2016-01-21
JP2014511347A (ja) 2014-05-15
US20120190867A1 (en) 2012-07-26
CN103443067B (zh) 2015-04-22
JP5952305B2 (ja) 2016-07-13
IL227592A (en) 2015-05-31
ES2613709T3 (es) 2017-05-25
TW201235336A (en) 2012-09-01
CN103443067A (zh) 2013-12-11
IL227592A0 (en) 2013-09-30

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