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Cinnamide compound synthesizing process

A technology for cinnamamide and compound, which is applied in the field of synthesizing cinnamamide compounds, can solve the problems of low synthesis efficiency, large environmental pollution, large energy consumption and the like, and achieves the effects of saving time, reducing reaction procedures and saving energy.

Inactive Publication Date: 2006-03-01
ZHEJIANG UNIV
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Problems solved by technology

[0015] The above synthetic reaction method is referred to as a linear synthetic method in organic synthesis, and its reaction is by gradually adding molecular fragments to synthesize the final product. Compared with another kind of synthetic method (formula C), which is called convergent in organic synthesis, Its total yield is relatively low, and the synthesis efficiency is also low
Moreover, all the reactions in the above synthesis method need to be carried out in an organic solvent, and almost every step of the reaction product needs to be separated and purified, so there are problems such as complex procedures, large energy consumption and large environmental pollution.

Method used

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  • Cinnamide compound synthesizing process

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Experimental program
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Effect test

Embodiment 1

[0040] Suspend 104.7 mg (0.54 mmol, 1.5 equivalents) of N-n-butyl α-bromoacetamide, 37 mg (0.35 mmol, 1.0 equivalents) of benzaldehyde, and 142 mg (0.54 mmol, 1.5 equivalents) of triphenylphosphine in a solution containing Lithium hydroxide 26 milligrams (0.65mmol, 1.8 equivalent) and lithium chloride water (5ml) solution of 1.2 molar concentration, reflux reaction 10 minutes, reaction solution is cooled to room temperature then, extract with ethyl acetate (10ml * 3) , the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain a yellow oil, 69 mg of N-n-butyl cinnamic acid, the yield was 96%, and the E / Z ratio was 86 / 14.

[0041] (E-isomer) 1 H NMR (400MHz, CDCl 3 )δ7.61(d, J=15.6Hz, 1H), 7.48-7.46(m, 2H), 7.34-7.30(m, 3H), 6.45(d...

Embodiment 2

[0043] 194 mg (1.00 mmol, 1.8 equivalents) of N-n-butyl α-bromoacetamide and 78 mg (0.56 mmol, 1.0 equivalents) of 4-chlorobenzaldehyde, 262 mg (1.00 mmol, 1.8 equivalents) of triphenylphosphine Suspended in lithium hydroxide 52 mg (1.23 mmol, 2.1 equivalents) and 1.2 molar lithium chloride water (5 ml) solution, refluxed for 10 minutes. Aftertreatment is with embodiment 1. The crude product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3: 1) to obtain a white solid (mp.118-120°C), 132 mg of N-n-butyl-3-phenylacrylamide, and the yield was 100% with an E / Z ratio of 86 / 14.

[0044] (E-isomer) 1 H NMR (400MHz, CDCl 3 )δ7.57(d, J=16.0Hz, 1H), 7.41(d, J=7.6Hz, 2H), 7.32(d, J=7.6Hz, 2H), 6.37(d, J=16.0Hz, 1H) , 5.77(bs, 1H), 3.41-3.36(m, 2H), 1.59-1.51(m, 2H), 1.43-1.34(m, 2H), 0.96-0.92(t, J=7.2Hz, 3H).( Z-isomer) 1 HNMR (400MHz, CDCl 3 )δ7.41(d, J=8.4Hz, 2H), 7.29(d, J=8.4Hz, 2H), 6.65(d, J=12.4Hz, 1H), 5.97(d, J=12.4Hz, 1H...

Embodiment 3

[0046] 194 mg (1.00 mmol, 1.8 equivalents) of N-n-butyl α-bromoacetamide and 84 mg (0.56 mmol, 1.0 equivalents) of 4-nitrobenzaldehyde, 262 mg (1.00 mmol, 1.8 equivalents) of triphenylphosphine ) was suspended in lithium chloride water (5ml) solution containing lithium hydroxide 52 mg (1.23mmol, 2.1 equivalents) and 1.2 molar concentration, and refluxed for 5 minutes. Aftertreatment is with embodiment 1. The crude product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a yellow solid (mp.126-128°C), N-n-butyl-3-(4-nitrophenyl)acrylamide 112 mg, 80.5% yield, E / Z ratio 95 / 5.

[0047] (E-isomer) 1 H NMR (400MHz, CDCl 3 )δ8.19(d, J=8.4Hz, 2H), 7.65(d, J=15.6Hz, 1H), 7.63(d, J=8.4Hz, 1H), 6.55(d, J=15.6Hz, 1H) , 5.98(bs, 1H), 3.42-3.37(m, 2H), 1.58-1.52(m, 2H), 1.41-1.36(m, 2H), 0.96-0.91(t, J=7.2Hz, 3H).

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Abstract

The present invention discloses cinnamide compound synthesizing process. Inside water phase and in the presence of triphenyl phosphine, inorganic alkali and inorganic salt, bromoacetylamide and aromatic aldehyde react to synthesize cinnamide compound. During the convergent synthesis process, bromoacetylamide and triphenyl phosphine first react to produce quarternary ammonium salt as intermediate, the quarternary ammonium salt then reacts with alkali to produce corresponding ylide, and the ylide finally reacts with aromatic aldehyde to produce the cinnamide compound. The intermediate needs no separation, and this results in less reaction steps, short reaction period, low power consumption, high yield and reduced effluent. In addition, the present invention performs reaction in water phase to avoid use harmful expensive organic solvent.

Description

technical field [0001] The invention relates to a method for synthesizing cinnamamide compounds. Especially in the presence of triphenylphosphine, inorganic base and inorganic salt in the aqueous phase, the method for synthesizing cinnamic amide compounds by reacting α-bromoacetamide and aromatic aldehyde. Background technique [0002] Cinnamamide compounds have been used clinically as drugs for a long time. Cinpropazide blocks Ca 2+ As a carrier, it is used for coronary heart disease and bronchospasm asthma, and can also prevent Ca in mast cell membranes 2+ Carrier to prevent degranulation allergies. Cinepazet (cinepazet) has an anti-anginal effect, and cinepazide (cinepazide) has a vasodilator effect, and is used for the treatment of hypertension. Cinnamon bromide (cinromide) compounds have anticonvulsant effect and can be used to treat epilepsy. And cinmetacin has a good anti-inflammatory effect. [0003] In recent years, some medicinal plants have been found to con...

Claims

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Application Information

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IPC IPC(8): C07C233/11C07C231/12C07C235/34C07D307/14
Inventor 吴金龙岳从永戴伟民
Owner ZHEJIANG UNIV
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