Title:
PROCESS FOR PREPARING TERTIARY AMINES
Document Type and Number:
WIPO Patent Application WO/2023/115292
Kind Code:
A1
Abstract:
Provided is a simple and environmentally friendly process for preparing tertiary amines by the aminomethylation of alkenes. This process features relatively mild reaction conditions and no metal catalyst.
Inventors:
WISCHERT RAPHAEL JOHANNES (CN)
PERA TITUS MARC (FR)
JEROME FRANCOIS (FR)
PENG GONGMING (CN)
STREIFF STEPHANE (FR)
PERA TITUS MARC (FR)
JEROME FRANCOIS (FR)
PENG GONGMING (CN)
STREIFF STEPHANE (FR)
Application Number:
PCT/CN2021/139864
Publication Date:
June 29, 2023
Filing Date:
December 21, 2021
Export Citation:
Assignee:
RHODIA OPERATIONS (FR)
CENTRE NAT RECH SCIENT (FR)
UNIV POITIERS (FR)
CENTRE NAT RECH SCIENT (FR)
UNIV POITIERS (FR)
International Classes:
C07C209/60; C07C209/28; C07C211/02
Domestic Patent References:
| WO2019219942A1 | 2019-11-21 | |||
| WO2001064621A1 | 2001-09-07 |
Foreign References:
| CN1918110A | 2007-02-21 | |||
| US20050215825A1 | 2005-09-29 | |||
| EP2975019A1 | 2016-01-20 | |||
| TWI228498B | 2005-03-01 | |||
| CN101056844A | 2007-10-17 | |||
| CN102786420A | 2012-11-21 | |||
| CN102070458A | 2011-05-25 | |||
| CN1538950A | 2004-10-20 |
Other References:
AARON TROWBRIDGE ET.AL.: "Multicomponent synthesis of tertiary alkylamines by photocatalytic olefin-hydroaminoalkylation", NATURE, vol. 561, 26 September 2018 (2018-09-26), pages 522 - 527, XP036600616, DOI: 10.1038/s41586-018-0537-9
KUNJANPILLAI RAJESH ET.AL.: "One-pot three component a-aminoalkylation of conjugated nitroalkenes and nitrodienes", TETRAHEDRON LETTERS, vol. 51, 11 December 2009 (2009-12-11), pages 846 - 849, XP026824877
ABONIA RODRIGO, CASTILLO JUAN, INSUASTY BRAULIO, QUIROGA JAIRO, NOGUERAS MANUEL, COBO JUSTO: "Efficient Catalyst-Free Four-Component Synthesis of Novel γ-Aminoethers Mediated by a Mannich Type Reaction", ACS COMBINATIONAL SCIENCE, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 1, 14 January 2013 (2013-01-14), US , pages 2 - 9, XP093074739, ISSN: 2156-8952, DOI: 10.1021/co300105t
SCHMIDLE CLAUDE J, MANSFIELD RICHARD C: "The Aminomethylation of Olefins. I. The Reaction of Secondary Amines, Formaldehyde, and Olefins", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 77, 1 September 1955 (1955-09-01), pages 4636 - 4638, XP093074738, DOI: 10.1021/ja01622a058
THEODORE COHEN: "Competing Hydride Transfer and Ene Reactions in the Aminoalkylation of 1-Alkenes with N，N-Dimethylmethyleniminium Ions. A Literature Correction", J. ORG. CHEM., vol. 48, 31 December 1983 (1983-12-31), pages 4531 - 4537, XP002524228
DANIEL KAISER; VERONICA TONA; CARLOS R. GONÇALVES; SAAD SHAABAN; ALBERTO OPPEDISANO; NUNO MAULIDE: "A General Acid‐Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 58, no. 41, 4 September 2019 (2019-09-04), Hoboken, USA, pages 14639 - 14643, XP072095444, ISSN: 1433-7851, DOI: 10.1002/anie.201906910
MANNINEN， KALLE: "Hydride transfer reaction products in the aminomethylation of styrene", ACTA CHEMICA SCANDINAVICA， SERIES B: ORGANIC CHEMISTRY AND BIOCHEMISTRY, vol. B40, no. 3, 31 December 1986 (1986-12-31), pages 190 - 195, XP008105598
KUNJANPILLAI RAJESH ET.AL.: "One-pot three component a-aminoalkylation of conjugated nitroalkenes and nitrodienes", TETRAHEDRON LETTERS, vol. 51, 11 December 2009 (2009-12-11), pages 846 - 849, XP026824877
ABONIA RODRIGO, CASTILLO JUAN, INSUASTY BRAULIO, QUIROGA JAIRO, NOGUERAS MANUEL, COBO JUSTO: "Efficient Catalyst-Free Four-Component Synthesis of Novel γ-Aminoethers Mediated by a Mannich Type Reaction", ACS COMBINATIONAL SCIENCE, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 1, 14 January 2013 (2013-01-14), US , pages 2 - 9, XP093074739, ISSN: 2156-8952, DOI: 10.1021/co300105t
SCHMIDLE CLAUDE J, MANSFIELD RICHARD C: "The Aminomethylation of Olefins. I. The Reaction of Secondary Amines, Formaldehyde, and Olefins", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 77, 1 September 1955 (1955-09-01), pages 4636 - 4638, XP093074738, DOI: 10.1021/ja01622a058
THEODORE COHEN: "Competing Hydride Transfer and Ene Reactions in the Aminoalkylation of 1-Alkenes with N，N-Dimethylmethyleniminium Ions. A Literature Correction", J. ORG. CHEM., vol. 48, 31 December 1983 (1983-12-31), pages 4531 - 4537, XP002524228
DANIEL KAISER; VERONICA TONA; CARLOS R. GONÇALVES; SAAD SHAABAN; ALBERTO OPPEDISANO; NUNO MAULIDE: "A General Acid‐Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 58, no. 41, 4 September 2019 (2019-09-04), Hoboken, USA, pages 14639 - 14643, XP072095444, ISSN: 1433-7851, DOI: 10.1002/anie.201906910
MANNINEN， KALLE: "Hydride transfer reaction products in the aminomethylation of styrene", ACTA CHEMICA SCANDINAVICA， SERIES B: ORGANIC CHEMISTRY AND BIOCHEMISTRY, vol. B40, no. 3, 31 December 1986 (1986-12-31), pages 190 - 195, XP008105598
Attorney, Agent or Firm:
CHINA PATENT AGENT (H.K.) LTD. (CN)
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