JP6861714B2 - オルトカルボン酸エステルを用いたアミンの還元的アルキル化 - Google Patents
オルトカルボン酸エステルを用いたアミンの還元的アルキル化 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- 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
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- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
前記式中、基R及びR1は、互いに独立して、H、又は直鎖であるか、任意の所望の炭素原子上で1つ以上の置換基で提供される(C1〜C24)−アルキル基、(C3〜C20)−シクロアルキル基、(C2〜C13)−ヘテロシクロアルキル基、(C6〜C14)−アリール基もしくは(C3〜C13)−ヘテロアリール基からなる群から選択され、但し、RおよびR1は同時にHではなく、基RとR1は、任意に、飽和又は一不飽和もしくは多不飽和の(C2〜C18)−アルキレン又は(C2〜C18)−ヘテロアルキレン架橋を形成して、合計3〜20個の環原子を有する環を形成することができ、かつ
R2は、H、(C1〜C24)−アルキル、(C3〜C20)−シクロアルキル、(C2〜C13)−ヘテロシクロアルキル、(C6〜C14)−アリール、(C3〜C13)−ヘテロアリールからなる群から選択され、かつ
R3、R4及びR5は、互いに独立して、H、(C1〜C24)−アルキル、(C3〜C8)−シクロアルキル又は(C6〜C14)−アリールからなる群から選択され、
ここで、基R2とR3、及びR3とR4の双方は、互いに独立して、飽和又は一不飽和もしくは多不飽和の(C2〜C18)−アルキレン又は(C2〜C18)−ヘテロアルキレン架橋を形成して、合計3〜20個の環原子を有する環を形成することができる。
−OH、
−(C1〜C8)−アルキルオキシ
−COOH、
−NH({C1〜C8}−アシル)、
−NH({C1〜C8}−アシルオキシ)、
−N((C1〜C20)−アルキル)({C1〜C8}−アシル)、
−N({C6〜C14}−アリール)({C1〜C8}−アシル)、
−N({C6〜C14}−アラルキル)({C1〜C8}−アシル)、
−N({C1〜C8}−アシル)2、
−NH3 +、
−NH({C1〜C20}−アルキル)2 +、
−NH({C6〜C14}−アリール)2 +、
−NH({C6〜C14}−アラルキル)2 +、
−NH({C1〜C20}−アルキル)({C6〜C14}−アリール)+、
−N({C6〜C14}−アリール)({C1〜C20}−アルキル)2 +、
−N({C6〜C14}−アリール)2({C1〜C20}−アルキル)+、
−O−C(=O)−O−{C1〜C20}−アルキル、
−O−C(=O)−O−{C6〜C14}−アリール、
−O−C(=O)−O−{C6〜C14}−アラルキル、
−NH−C(=O)−O−{C1〜C20}−アルキル、
−NH−C(=O)−O−{C6〜C14}−アリール、
−NH−C(=O)−O−{C6〜C14}−アラルキル、
−O−C(=O)−NH−{C1〜C20}−アルキル、
−O−C(=O)−NH−{C6〜C14}−アリール、
−O−C(=O)−NH−{C6〜C14}−アラルキル、
−CN、
−SO2−O−{C1〜C20}−アルキル、
−SO2−O−{C6〜C14}−アリール、
−SO2−O−{C6〜C14}−アラルキル、
−SO2−{C1〜C20}−アルキル、
−SO2−{C6〜C14}−アリール、
−SO2−{C6〜C14}−アラルキル、
−SO−{C1〜C20}−アルキル、
−SO−{C6〜C14}−アリール、
−SO−{C6〜C14}−アラルキル、
−Si({C1〜C20}−アルキル)3、
−Si({C6〜C14}−アリール)3、
−Si({C6〜C14}−アリール)({C1〜C20}−アルキル)2、
−Si({C6〜C14}−アリール)2({C1〜C20}−アルキル)、
−{C1〜C20}−ペルフルオロアルキル、
−PO(O−{C1〜C20}−アルキル)2、
−PO(O−{C6〜C14}−アリール)2、
−PO(O−{C1〜C20}−アルキル)(O−{C6〜C14}−アリール)、
−PO({C1〜C20}−アルキル)2、
−PO({C6〜C14}−アリール)2、
−PO({C1〜C20}−アルキル)({C6〜C14}−アリール)
である。
オルトカルボン酸エステルによるアミンの還元的アルキル化のための一般的方法
オートクレーブを、触媒(アミンのモル量に対して1mol%)で満たし、アルゴンで洗い流し、そしてメタノール10ml中のアミン(0.1mol)およびオルトカルボン酸エステル(0.11〜0.3mol)の溶液、及びメタノール(又はエタノール)中0.2Mの無水p−トルエンスルホン酸の溶液0.5mlを供給した。その混合物を120℃まで加熱し、水素を40barまで注入し、そしてその混合物を、水素吸収が検出されなくなるまで(0.2〜6時間)一定圧力で撹拌した。触媒から濾別した後、その濾過物を蒸留した。
Claims (12)
- オルトカルボン酸エステルとアミン又はアンモニアと水素とを、水素化触媒の存在下で反応させることによりアミン又はアンモニアをN−アルキル化する方法。
- 酸の存在下で反応を実施する、請求項1に記載の方法。
- 使用される酸とアミンとのモル比0.01:100〜10:100の範囲で反応を実施する、請求項2に記載の方法。
- 使用される水素化触媒とアミンとのモル比1:10〜1:100000の範囲で反応を実施する、請求項1から3までのいずれか1項に記載の方法。
- 0.1bar〜200barの範囲の水素分圧で反応を実施する、請求項1から4までのいずれか1項に記載の方法。
- 20℃〜200℃の温度範囲で反応を実施する、請求項1から5までのいずれか1項に記載の方法。
- 水素化触媒が、不均一系水素化触媒である、請求項1から6までのいずれか1項に記載の方法。
- 不均一系水素化触媒が、少なくとも1種の活性金属を含む、請求項7に記載の方法。
- 活性金属が、元素の周期表のVII B族及び/又はVIII B族の金属である、請求項8に記載の方法。
- 溶媒中で反応を実施する、請求項1から9までのいずれか1項に記載の方法。
- 溶媒が、炭化水素、塩化炭化水素、エーテル、エステル及びアルコールからなる群から選択される、請求項10に記載の方法。
- 溶媒を使用せずに反応を実施する、請求項1から9までのいずれか1項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16154092.7A EP3202758A1 (de) | 2016-02-03 | 2016-02-03 | Reduktive alkylierung von aminen mit orthocarbonsäureestern |
EP16154092.7 | 2016-02-03 | ||
PCT/EP2017/051313 WO2017133913A1 (en) | 2016-02-03 | 2017-01-23 | Reductive alkylation of amines with orthocarboxylic acid esters |
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JP2019504092A JP2019504092A (ja) | 2019-02-14 |
JP6861714B2 true JP6861714B2 (ja) | 2021-04-21 |
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US (1) | US10781164B2 (ja) |
EP (2) | EP3202758A1 (ja) |
JP (1) | JP6861714B2 (ja) |
CN (1) | CN108602753B (ja) |
WO (1) | WO2017133913A1 (ja) |
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CN111470954A (zh) * | 2020-04-12 | 2020-07-31 | 上海泰初化工技术有限公司 | 一种原羧酸酯的合成方法 |
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US5270464A (en) * | 1989-03-14 | 1993-12-14 | Janssen Pharmaceutica N.V. | Anti-HIV-1 tetrahydroimidazo[1,4]benzodiazepin-2-(thi) ones |
CN1029848C (zh) * | 1989-02-23 | 1995-09-27 | 詹森药业有限公司 | 四氢咪唑并[1,4]苯并二氮杂䓬-2-硫酮的制备方法 |
DE19933611A1 (de) * | 1999-07-17 | 2001-01-18 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Aminen durch homogen katalysierte reduktive Aminierung von Carbonylverbindungen |
DE10138140A1 (de) | 2001-08-09 | 2003-02-20 | Degussa | Verfahren zur Herstellung von Aminen durch reduktive Aminierung von Carbonylverbindungen unter Transfer-Hydrierungsbedingungen |
EP1595888A1 (en) | 2004-05-11 | 2005-11-16 | Degussa AG | Cycloolefin phosphine ligands and their use in catalysis |
DE102005014055A1 (de) | 2005-03-23 | 2006-09-28 | Degussa Ag | Unsymmetrisch substituierte Phospholankatalysatoren |
DE102005014822A1 (de) | 2005-03-30 | 2006-10-05 | Degussa Ag | Verfahren zur Herstellung aromatischer Aldehyde |
FR2888238B1 (fr) * | 2005-07-07 | 2007-09-07 | Servier Lab | Nouveaux derives 1h-indole-pyridinecarboxamides et 1h-indole-piperidinecarboxamide, leur procede de preparation et les compositions pharceumatiques qui les contiennent. |
US20070213540A1 (en) | 2006-03-09 | 2007-09-13 | Degussa Ag | Process for the hydrogenation of imines |
EP1894938A1 (en) | 2006-08-31 | 2008-03-05 | Evonik Degussa GmbH | New cyclopentadienyl, indenyl or fluorenyl substituted phosphine compounds and their use in catalytic reactions |
BRPI0911432B1 (pt) | 2008-04-08 | 2018-01-02 | Evonik Degussa Gmbh | COMPLEXOS DE Ru-CARBENO, SEUS PROCESSOS DE PREPARAÇÃO E SEU USO |
CA2814930C (en) * | 2010-11-05 | 2019-02-12 | Otsuka Agritechno Co., Ltd. | Ethynylphenylamidine compound or salt thereof, method for producing same, and fungicide for agricultural and horticultural use |
EP2868652A1 (de) | 2013-11-05 | 2015-05-06 | Evonik Industries AG | Katalytische Hydrierung zur Herstellung von Aminen aus Amidacetalen, Keten-N,O-acetalen oder Esterimiden |
EP2868643A1 (de) * | 2013-11-05 | 2015-05-06 | Evonik Industries AG | Katalytische Hydrierung zur Herstellung von Aminen aus Carbonsäureamiden, Carbonsäurediamiden, Di-, Tri- oder Polypeptiden oder Peptidamiden |
EP2933274A1 (de) | 2014-04-16 | 2015-10-21 | Evonik Degussa GmbH | Verfahren zur Herstellung von Polymeren mittels ringöffnender Polymerisation |
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2016
- 2016-02-03 EP EP16154092.7A patent/EP3202758A1/de not_active Withdrawn
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2017
- 2017-01-23 EP EP17701839.7A patent/EP3411353B1/en active Active
- 2017-01-23 CN CN201780009192.4A patent/CN108602753B/zh active Active
- 2017-01-23 JP JP2018540374A patent/JP6861714B2/ja active Active
- 2017-01-23 US US16/074,306 patent/US10781164B2/en active Active
- 2017-01-23 WO PCT/EP2017/051313 patent/WO2017133913A1/en active Application Filing
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Publication number | Publication date |
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US20200231537A1 (en) | 2020-07-23 |
WO2017133913A1 (en) | 2017-08-10 |
EP3202758A1 (de) | 2017-08-09 |
EP3411353B1 (en) | 2020-03-04 |
US10781164B2 (en) | 2020-09-22 |
CN108602753B (zh) | 2021-05-11 |
CN108602753A (zh) | 2018-09-28 |
EP3411353A1 (en) | 2018-12-12 |
JP2019504092A (ja) | 2019-02-14 |
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