Method for preparing N-1, 5-diaryl-4-pentene-1-acetamide compound

A compound and diaryl technology, applied in pharmaceutical chemical intermediates and related chemical fields, can solve problems such as limited application, and achieve the effects of simple operation and cheap and easy-to-obtain starting materials

Active Publication Date: 2019-05-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of certain types of acidic substances that have useful applications such as medicines or other organics. It involves only one type of material - called an initiator molecule – with specific functions like reducing unwanted side reactions during manufacturing process. By adding these activators into reaction mixtures containing different reactants at once, we get high yields from each step without generating any waste product. Additionally, there may also be some special groups added onto the resulting amides through silylation chemistry techniques. Overall, our technical effect will improve efficiency and reduce costs associated with producing new kinds of active ingredients.

Problems solved by technology

This patented technical problem addressed by our patents relates to improving methods for producing various types of molecules that contain one or more unsymmetrically substituted carboxilic acid structures called naphthaleneimino acids (N1-4). These molecular entities include butterlenol hydrocarbon rings, pyranones, cyclohexane ring systems, quaternary salt structure containing sulfur atoms, etcetera. Existing techniques involve expensive procedures like reaction between different components at specific temperatures, complicated processes involving multiple step operations, limited applications due to their poor solubility, difficulty in purifying these products from impurities during production process, and potential safety concerns associated therewith.

Method used

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  • Method for preparing N-1, 5-diaryl-4-pentene-1-acetamide compound
  • Method for preparing N-1, 5-diaryl-4-pentene-1-acetamide compound
  • Method for preparing N-1, 5-diaryl-4-pentene-1-acetamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of trans-N-1,5-diaryl-4-pentene-1-acetamide

[0048] In a 25mL reactor, add cuprous chloride (1.49mg, 0.015mmol), silver hexafluoroantimonate (20.6mg, 0.06mmol), 1,4-bis(diphenylphosphine)butane (7.68mg, 0.018mmol ), cinnamyl alcohol (0.040g, 0.3mmol), 4-nitrobenzoic acid (10.02mg, 0.06mmol), after nitrogen replacement 3 times, add 0.3mL acetonitrile, after stirring at room temperature for 10 minutes, add styrene (0.094 g, 0.9 mmol), stirred at 105°C for 16 hours. Column chromatography separation (silica gel, 200-300 mesh; developer, petroleum ether / ethyl acetate = 3 / 2) to obtain trans-N-1,5-diaryl-4-pentene-1-acetamide 0.069 g, yield 82%.

[0049] trans-N-1,5-diaryl-4-pentene-1-acetamide white solid; 1 H NMR (400MHz, CDCl 3 ):δ7.35–7.32(m,4H),7.30–7.25(m,5H),7.18(t,J=6.9Hz,1H),6.35(d,J=15.9Hz,1H),6.18(dt, J=15.9,6.8Hz,1H),5.95(bs,1H),5.02(q,J=7.6Hz,1H),2.23–2.15(m,2H),2.05–1.98(m,1H),1.96(s ,3H),1.94–1.82(m,1H). 13 C NMR (100MHz, CDCl 3

Embodiment 2

[0050] Example 2: Synthesis of trans-N-5-(4-bromophenyl)-1-phenyl-4-pentene-1-acetamide

[0051] Operation is the same as in Example 1, by reacting trans-3-(4-bromophenyl)-2-propen-1-alcohol and styrene in acetonitrile to obtain trans-N-5-(4-bromophenyl)- 0.086 g of 1-phenyl-4-pentene-1-acetamide, yield 80%.

[0052] trans-N-5-(4-bromophenyl)-1-phenyl-4-pentene-1-acetamide yellow solid; 1 H NMR (500MHz, CDCl 3 ):δ7.40–7.26(m,7H),7.16(d,J=8.4Hz,2H),6.28(d,J=15.9Hz,1H),6.17(dt,J=15.9,6.7Hz,1H) ,5.78(d,J=7.7Hz,1H),5.02(q,J=7.6Hz,1H),2.22–2.15(m,2H),2.05–1.99(m,1H),1.97(s,3H), 1.96–1.89(m,1H). 13 C NMR (125MHz, CDCl 3 ):δ169.2,141.8,136.5,131.5,130.3,129.4,128.8,127.6,127.5,126.7,120.6,53.2,35.5,29.7,23.5.IR(KBr):3256,3069,2924,2852,1950,14945, ,1486,1278,1178,1058,1030,966,700,640cm -1 .HRMS(EI):calcd for C 19 h 20 BrNO[M] + :357.0728, and 359.0708 Found 357.0723 and 359.0701.

Embodiment 3

[0053] Example 3: Synthesis of trans-N-1-phenyl-5-(o-tolyl)-4-pentene-1-acetamide

[0054] Operation is the same as in Example 1, by reacting trans-3-(o-tolyl)-2-propen-1-alcohol and styrene in acetonitrile to obtain trans-N-1-phenyl-5-(o-tolyl) -4-pentene-1-acetamide 0.066g, yield 75%.

[0055] trans-N-1-phenyl-5-(o-tolyl)-4-pentene-1-acetamide brown solid; 1 H NMR (400MHz, CDCl 3 ):δ7.36–7.25(m,6H),7.15–7.10(m,3H),6.54(d,J=15.8Hz,1H),6.05(dt,J=15.8,6.8Hz,1H),5.90( bs,1H),5.04(q,J=7.6Hz,1H),2.32(s,3H),2.31–2.17(m,2H),2.05–2.00(m,1H),1.97(s,3H),1.95 –1.89(m,1H). 13 C NMR (125MHz, CDCl 3 ): δ169.0, 138.9, 137.6, 137.2, 130.5, 129.5, 129.4, 128.5, 126.9, 126.6, 126.0, 53.0, 35.6, 29.8, 23.5, 21.0.IR(KBr): 3260, 3047, 3033, 2915, 2951, ,1644,1540,1409,1250,1178,1031,967,742,701cm -1 .HRMS(EI):C 20 h 23 NO[M] + :293.1780, Found293.1789.

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Abstract

The invention belongs to the technical field of pharmaceutical and chemical intermediates and related chemistry, and provides a preparation method of an N-1, 5-diaryl-4-pentene-1-acetamide compound. The preparation method comprises the following steps: taking a cinnamyl alcohol derivative as a raw material, under the action of copper salt, silver salt and an acid as shown in specification as co-catalysts and ligands, reacting with a styrene compound and a nitrile compound under the solvent-free condition of 80-120 DEG C; or reacting with the styrene compound directly in a nitrile solvent at the temperature of 80-120 DEG C, and reacting for 16 hours to obtain the N-1, 5-diaryl-4-pentene-1-acetamide compound. The preparation method is simple and convenient to operate, the starting materialsare cheap and easy to obtain, no by-product is generated, the possibility of industrialization is realized, and the N-1, 5-diaryl-4-pentene-1-acetamide compound is obtained in high yield; and the synthesized product can be further functionalized to obtain various compounds, and is applied to the development and research of natural products, functional materials and fine chemicals.

Description

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Claims

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Application Information

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Owner DALIAN UNIV OF TECH
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