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Method for synthesizing alkylamine derivative

A derivative, alkylamine technology, applied in the field of dehydrogenation reduction coupling reaction, can solve problems such as narrow applicability, poor atom economy, excess, etc., and achieve the effects of simple operation, avoidance of subsequent processing, and low price

Active Publication Date: 2021-07-13
WESTLAKE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the shortcomings of existing substrates such as narrow applicability, excessive use of metal reagents or reducing agents, and poor atom economy, the present invention provides a method to directly realize the alkylation reaction at the α-position of the amine, and the efficient construction has various Alkylamine Derivatives with Sexual Structure

Method used

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  • Method for synthesizing alkylamine derivative
  • Method for synthesizing alkylamine derivative
  • Method for synthesizing alkylamine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of N-(1,3-Diphenylpropyl)-4-methylbenzenesulfonamide

[0038]

[0039] In a nitrogen atmosphere, sequentially add raw material 1a (0.2mmol, 52.2mg), raw material 2a (0.4mmol, 41.6mg), KO t Bu(0.05mmol, 5.6mg), PhB(OH) 2 (0.05mmol, 6.1mg), Ni(cod) 2 (0.005mmol, 1.4mg), and PCy 3 (0.01mmol, 2.8mg), finally added Toluene (0.3mL), stirred at 120°C for 20 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3a with a yield of 93%, 67.8mg. 1 H NMR (500MHz, CDCl 3 )δ7.54(d,J=8.0Hz,2H),7.20–7.17(m,2H),7.14–7.08(m,4H),7.03–6.99(m,6H),6.01(d,J=8.0Hz ,1H),4.28(dd,J 1 =15.0Hz,J 2 =7.5Hz,1H),2.58–2.52(m,1H),2.49–2.43(m,1H),2.29(s,3H),2.12–2.05(m,1H),1.99–1.92(m,1H); 13 C NMR (125MHz, CDCl 3 )δ142.7,140.8,140.6,137.5,129.1,128.24,128.19,127.1,126.9,126.5,125.8,57.8,38.9,32.0,21.3; HRMS(ESI)m / z calcd.For C 22 h 23 NNaO 2 S[M+Na] +:388.1342,found:388.1345.

[0040] Scaled-up preparation...

Embodiment 2

[0043] Preparation of N-(1,3-Diphenylpropyl)methanesulfonamide

[0044]

[0045] In a nitrogen atmosphere, sequentially add raw material 1b (0.2mmol, 37.0mg), raw material 2a (0.4mmol, 41.6mg), KO t Bu(0.05mmol, 5.6mg), PhB(OH) 2 (0.05mmol, 6.1mg), Ni(cod) 2 (0.005mmol, 1.4mg), and PCy 3 (0.01mmol, 2.8mg), finally added Toluene (0.3mL), stirred at 120°C for 20 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3b with a yield of 96%, 55.5mg. 1 H NMR (500MHz, CDCl 3 )δ7.40–7.37(m,2H),7.33–7.25(m,2H),7.19–7.17(m,1H),7.14(d,J=7.0Hz,2H),5.18–5.15(m,1H) ,4.46(dd,J 1 =15.0Hz,J 2 =7.5Hz,1H),2.71–2.65(m,1H),2.61–2.55(m,1H),2.53(s,3H),2.21–2.13(m,1H),2.10–2.03(m,1H); 13 C NMR (125MHz, CDCl 3 )δ141.2, 140.7, 129.0, 128.5, 128.4, 128.1, 126.7, 126.1, 57.9, 41.8, 39.2, 32.3.

Embodiment 3

[0047] Preparation of N-(1,3-Diphenylpropyl)-2,4,6-trimethylbenzonesulfonamide

[0048]

[0049] In an argon atmosphere, sequentially add raw material 1c (0.2mmol, 57.8mg), raw material 2a (0.4mmol, 41.6mg), KO t Bu(0.05mmol, 5.6mg), PhB(OH) 2 (0.05mmol, 6.1mg), Ni(cod) 2 (0.005mmol, 1.4mg), and PCy 3 (0.01mmol, 2.8mg), finally added Toluene (0.3mL), stirred at 120°C for 20 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3c with a yield of 98%, 77.0mg. 1 H NMR (500MHz, CDCl 3 )δ7.24–7.21(m,2H),7.17–7.11(m,4H),7.02(d,J=7.5Hz,2H),6.96–6.94(m,2H),6.77(s,2H),5.01 –4.98(m,1H),4.18(dd,J 1 =14.0Hz,J 2 =7.0Hz,1H),2.55–2.44(m,8H),2.23(s,3H),2.16–2.09(m,1H),2.05–1.98(m,1H); 13 C NMR (125MHz, CDCl 3 )δ141.9, 140.8, 140.3, 138.7, 134.3, 131.7, 128.37, 128.35, 128.32, 127.5, 126.3, 126.0, 57.6, 38.6, 32.0, 22.8, 20.8.

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Abstract

The invention discloses a method for synthesizing an alkylamine derivative. Hydrogen transfer in reactant amine is realized by using a metal nickel catalyst, and coupling reaction of the metal nickel catalyst and olefin is realized under the same catalytic system to construct alkylamine; and the reaction shows good compatibility to amine compounds, aryl and alkyl olefins, and the construction of chiral alkylamine is realized by using a chiral ligand. According to the method, an additional reducing agent does not need to be added as a hydrogen source, an additional guiding base does not need to be introduced, the scale is enlarged to the gram level, and the yield can still be kept.

Description

technical field [0001] The invention relates to the technical field of dehydrogenation reduction coupling reaction, in particular to a method for preparing alkylamine derivatives starting from ordinary non-guiding amines and olefins. Background technique [0002] Alkylamine structures widely exist in medicine, natural products, functional materials and many chiral ligands, and are an important class of organic synthesis building blocks and structural units. Therefore, how to efficiently prepare alkylamine derivatives with diverse structures has high research and application value. [0003] At present, alkylamine derivatives are mainly synthesized by the following methods: [0004] (1) Alkylamine derivatives are prepared by reduction reaction of imine or enamine. The reaction substrate imine or enamine is unstable, easy to decompose, and the synthesis is relatively inconvenient; and an excessive amount of reducing agent still needs to be used in the reduction. In addition,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/16C07C311/17C07C311/19C07C303/40C07D295/135C07C311/18C07D307/52C07D333/20C07D209/14C07D209/48C07D205/04C07D211/28C07D209/08C07D215/12C07F17/02C07F7/08
CPCC07C303/40C07D295/135C07D307/52C07D333/20C07D209/14C07D209/48C07D205/04C07D211/28C07D209/08C07D215/12C07F17/02C07F7/081C07F7/083C07C311/16C07C311/17C07C311/19C07C311/18
Inventor 石航燕小标李伦
Owner WESTLAKE UNIV
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