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A kind of preparation method of allylamine

A technology for allylamine and olefin, which is applied in the field of organic chemical synthesis, can solve the problems of a large number of metal reagents, large pollution, and difficulty in realizing industrialized production, and achieves the effects of good reaction selectivity, high yield and easy industrialization.

Inactive Publication Date: 2015-09-30
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
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Problems solved by technology

For example: Method 2, although the reaction conditions are mild, but requires pre-functionalization of the substrate and special ligands; Method 3, requires the use of more expensive alkynes as reaction raw materials; Method 4, requires a large amount of metal reagents, causing great pollution ; Method five, the substrate needs a guiding group, and the noble metal Rh is needed as a catalyst, which is difficult to realize industrial production

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  • A kind of preparation method of allylamine

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Effect test

Embodiment 1

[0034] Embodiment 1, the preparation of allylamine 3aa

[0035]

[0036] Styrene 1a (83.2 mg, 0.8 mmol), Pd(Xantphos)Cl 2 (15.1 mg, 5 mol %, 0.02 mmol), amine acetal 2a (162.4 mg, 0.4 mmol), under argon, 110 o C was reacted for 12 hours and separated by column chromatography (using a silica gel column; eluent: petroleum ether / ethyl acetate=100 / 1) to obtain pure allylamine 3aa. The product is a colorless liquid with a yield of 93%.

[0037] 1 H NMR (400 MHz, CDCl 3 ) δ 7.37-7.41 (m, 4H), 7.29-7.35 (m, 8H), 7.19-7.25 (m, 3H), 6.51 (d, J = 16.0 Hz, 1H), 6.26-6.33 (m, 1H ), 3.63 (s, 4H), 3.21 (dd, J 1 =1.2Hz, J 2 = 6.4 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.7, 137.3, 132.5, 128.8, 128.6, 128.3, 127.8, 127.3, 126.9, 126.3, 58.0, 55.8; HRMS (ESI) calcd. 23 h 24 N [M+1]: 314.1903, found: 314.1909.

Embodiment 2

[0038] Embodiment 2, the preparation of allylamine 3aa

[0039]

[0040] Styrene 1a (83.2 mg, 0.8 mmol), Pd(Xantphos)(CH 3 EN) 2 (OTf) 2 (21.3 mg, 5 mol %, 0.02 mmol), amine acetal 2a (162.4 mg, 0.4 mmol), under argon, 110 o C was reacted for 12 hours and separated by column chromatography (using a silica gel column; eluent: petroleum ether / ethyl acetate=100 / 1) to obtain pure allylamine 3aa. The product is a colorless liquid with a yield of 96%.

Embodiment 3

[0041] Embodiment 3, the preparation of allylamine 3aa

[0042]

[0043] Styrene 1a (83.2 mg, 0.8 mmol), Pd(Xantphos)(CH 3 EN) 2 (OTf) 2 (4.3 mg, 1 mol %, 0.004 mmol), amine acetal 2a (162.4 mg, 0.4 mmol), isopropanol (1.5 mL) were added to the reaction flask, under argon, 110 o C was reacted for 12 hours and separated by column chromatography (using a silica gel column; eluent: petroleum ether / ethyl acetate=100 / 1) to obtain pure allylamine 3aa. The product is a colorless liquid with a yield of 90%.

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Abstract

The invention discloses a method for preparing allyl amine and belongs to the technical field of organic chemical synthesis. The method comprises the following steps: preparing a catalyst by using a metal palladium salt or nickel salt and a phosphine ligand, reacting two components such as olefin and amine acetal or three components such as olefin, amine and aldehyde at the temperature of 25-140 DEG C, and preparing the allyl amine at high efficiency through one step. The reaction raw materials and catalyst are low in price and readily available, the synthetic process is simple, and the synthetic cost is greatly reduced; the reaction conditions are mild, the yield is high, and industrialization is easily realized; and the reaction raw materials and catalyst are clean and non-toxic and slight in environmental pollution. The reaction can be used for efficiently preparing cinnarizine, naftifine and terbinafine and has good market application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of allylamine. Background technique [0002] Allylamine is a common pharmacophore, which widely exists in various natural products and synthetic drugs with physiological activity, and is also a fragment of various functional materials. For example, 1-benzhydryl-trans-cinnamylpiperazine (cinnarizine, also known as cerebral overflow), is a calcium antagonist peripheral vasodilator drug, which can relieve vasospasm and prevent vascular embrittlement; Naftifine is a broad-spectrum antifungal drug with low toxicity; Terbinafine is a broad-spectrum antifungal drug. Due to the special use of this type of compound, people have developed a large number of synthetic methods in recent years, and the common reported preparation methods are as follows: [0003] Method 1: Add cinnamyl chloride dropwise to piperazine hydrochloride ethanol solution, and th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/29
Inventor 黄汉民谢银君
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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