WO2024153910A3 - Flow synthesis of amines - Google Patents
Flow synthesis of amines Download PDFInfo
- Publication number
- WO2024153910A3 WO2024153910A3 PCT/GB2024/050078 GB2024050078W WO2024153910A3 WO 2024153910 A3 WO2024153910 A3 WO 2024153910A3 GB 2024050078 W GB2024050078 W GB 2024050078W WO 2024153910 A3 WO2024153910 A3 WO 2024153910A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- flow
- formula
- electrochemical
- synthesis
- heterocyclic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/05—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/13—Single electrolytic cells with circulation of an electrolyte
- C25B9/15—Flow-through cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A two step synthesis of electrochemical flow synthesis of nitroamines, comprising the method of electrochemical continuous flow nitrosylation of amines for the synthesis of N-nitrosamines, comprising the steps of: i). preparing input flow reagent A in a first solvent, comprising the amine compound of Formula (I), wherein R1 and R2 are independently selected fromialkyl, aryl, phenyl, cycloakyl, heterocyclic, heterocyclic aromatic, or together form cycloakyl, heterocyclic, heterocyclic aromatic; ii). preparing input flow reagent B a nitrite salt in aqueous solution; iii). causing the input flow reagents A and B to enter a continuous electrochemical flow reactor provided with electrodes for electrolysis, at a flow rate, to furnish a reaction solution comprising a N-Nitrosamines of Formula (II). and the subsequent step of causing the compound of Formula II to be subjected 20 to continuous flow electrochemical oxidation to form a compound of Formula (III).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2024210528A AU2024210528A1 (en) | 2023-01-19 | 2024-01-12 | Flow synthesis of amines |
| EP24701276.8A EP4652309A2 (en) | 2023-01-19 | 2024-01-12 | Flow synthesis of amines |
| IL322150A IL322150A (en) | 2023-01-19 | 2024-01-12 | Flow synthesis of amines |
| KR1020257026932A KR20250137625A (en) | 2023-01-19 | 2024-01-12 | Amine flow synthesis |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB2300801.4A GB202300801D0 (en) | 2023-01-19 | 2023-01-19 | Flow synthesis |
| GB2300801.4 | 2023-01-19 | ||
| GB2317757.9 | 2023-11-21 | ||
| GB2317757.9A GB2626410A (en) | 2023-01-19 | 2023-11-21 | Flow synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2024153910A2 WO2024153910A2 (en) | 2024-07-25 |
| WO2024153910A3 true WO2024153910A3 (en) | 2024-08-29 |
Family
ID=89662160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2024/050078 Ceased WO2024153910A2 (en) | 2023-01-19 | 2024-01-12 | Flow synthesis |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP4652309A2 (en) |
| KR (1) | KR20250137625A (en) |
| AU (1) | AU2024210528A1 (en) |
| IL (1) | IL322150A (en) |
| WO (1) | WO2024153910A2 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180305830A1 (en) * | 2015-10-15 | 2018-10-25 | Covestro Deutschland Ag | Method for producing amino-functional aromatic compounds |
| WO2021214278A2 (en) * | 2020-04-24 | 2021-10-28 | Pharmazell Gmbh | Regioselective oxidation of heterocyclic alpha-amino amides |
| WO2022123216A1 (en) * | 2020-12-09 | 2022-06-16 | Bae Systems Plc | Flow synthesis of rdx |
| WO2023278766A1 (en) * | 2021-06-30 | 2023-01-05 | Wisconsin Alumni Research Foundation | Electrochemical reductive coupling of phenol derivatives |
-
2024
- 2024-01-12 AU AU2024210528A patent/AU2024210528A1/en active Pending
- 2024-01-12 IL IL322150A patent/IL322150A/en unknown
- 2024-01-12 KR KR1020257026932A patent/KR20250137625A/en active Pending
- 2024-01-12 EP EP24701276.8A patent/EP4652309A2/en active Pending
- 2024-01-12 WO PCT/GB2024/050078 patent/WO2024153910A2/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180305830A1 (en) * | 2015-10-15 | 2018-10-25 | Covestro Deutschland Ag | Method for producing amino-functional aromatic compounds |
| WO2021214278A2 (en) * | 2020-04-24 | 2021-10-28 | Pharmazell Gmbh | Regioselective oxidation of heterocyclic alpha-amino amides |
| WO2022123216A1 (en) * | 2020-12-09 | 2022-06-16 | Bae Systems Plc | Flow synthesis of rdx |
| WO2023278766A1 (en) * | 2021-06-30 | 2023-01-05 | Wisconsin Alumni Research Foundation | Electrochemical reductive coupling of phenol derivatives |
Non-Patent Citations (6)
| Title |
|---|
| GORSKI WALDEMAR ET AL: "Oxidation of N-nitrosamines at a ruthenium-based modified electrode in aqueous solutions", JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol. 389, no. 1-2, 1 June 1995 (1995-06-01), AMSTERDAM, NL, pages 123 - 128, XP093128936, ISSN: 1572-6657, DOI: 10.1016/0022-0728(95)03837-7 * |
| MASAICHIRO MASUI: "N-NITROSATION OF SECONDARY AMINES EFFECTED BY ELECTROCHEMICAL OXIDATION OF NITRITE ION IN WEAKLY BASIC MEDIA", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 36, no. 1, 1 January 1988 (1988-01-01), JP, pages 459 - 461, XP093154404, ISSN: 0009-2363, DOI: 10.1248/cpb.36.459 * |
| MASUI MASAICHIRO ET AL: "Electrochemical Oxidation of N-Nitrosodialkylamines : Mechanism of N-Nitramine and [beta]-Ketonitrosamine Formation", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 33, no. 7, 25 July 1985 (1985-07-25), JP, pages 2721 - 2730, XP093128935, ISSN: 0009-2363, DOI: 10.1248/cpb.33.2721 * |
| OHMORI HIDENOBU ET AL: "Electrochemical Oxidation of N-nitrosopiperidines: Dual Pathways for N-Nitramine Formation", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 34, no. 6, 25 August 1986 (1986-08-25), JP, pages 3079 - 3086, XP093128932, ISSN: 0009-2363, DOI: 10.1248/cpb.34.3079 * |
| ROJAN ALI ET AL: "Flow Electrochemistry for the N-Nitrosation of Secondary Amines", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 29, no. 32, 2 May 2023 (2023-05-02), pages n/a, XP072613239, ISSN: 0947-6539, DOI: 10.1002/CHEM.202300957 * |
| SNJEZANA MALJURIC: "Translating batch electrochemistry to single-pass continuous flow conditions: an organic chemist's guide", JOURNAL OF FLOW CHEMISTRY, vol. 10, no. 1, 17 February 2020 (2020-02-17), HU, pages 181 - 190, XP093154502, ISSN: 2062-249X, DOI: 10.1007/s41981-019-00050-z * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2024153910A2 (en) | 2024-07-25 |
| AU2024210528A1 (en) | 2025-07-31 |
| IL322150A (en) | 2025-09-01 |
| EP4652309A2 (en) | 2025-11-26 |
| KR20250137625A (en) | 2025-09-18 |
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