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Synthesis method of nitrogen nitrosation product of secondary amine

A synthesis method and nitrosation technology, applied in electrolytic organic production, electrolytic components, electrolytic process and other directions, can solve the problems of side reactions, harsh reaction conditions, long reaction time, etc., and achieve high yield and good substrate universality. , the effect of simple reaction process

Active Publication Date: 2020-06-05
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0003] Although there are many reports on this N-nitrosation, most of these methods have one or more of the following disadvantages: harsh reaction conditions, long reaction time, low product yield, heavy metal pollution and side reactions
However, it should be noted that performing N-nitrosation in an acid-free system remains a challenge

Method used

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  • Synthesis method of nitrogen nitrosation product of secondary amine
  • Synthesis method of nitrogen nitrosation product of secondary amine
  • Synthesis method of nitrogen nitrosation product of secondary amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of N-nitrosomorpholine

[0029]

[0030] In an oven-dried three-neck flask (25mL) equipped with a stirring bar, add morpholine (1.0mmol, 87mg), electrolyte n-Bu 4 NBF 4 (205mg, 0.6mmol) and ferric nitrate nonahydrate (2.0mmol, 0.808g). The three-necked flask is equipped with a graphite rod (Φ=6mm) as the anode, and a platinum plate electrode (10mm×10mm) as the cathode, and 16mL of CH 3 CN, then evacuated and flushed with nitrogen as a protective gas. The reaction mixture was stirred at reflux for 4 hours at a constant current of 12 mA at 70°C. When the reaction was completed, the reaction mixture was washed with water twice and extracted with ethyl acetate (10 mL×3). Then the organic layers were combined and washed with Na 2 SO 4 Concentrate in vacuo after drying, then obtain pure product by flash chromatography column, be light yellow oily liquid, yield rate is 92%, the NMR characteristic of this product is: 1 H NMR (500MHz, DMSO-d 6 )δ=4.26–4.16(m...

Embodiment 2

[0032] Synthesis of N-nitrosomorpholine

[0033]

[0034] The reaction steps are exactly the same as in Example 1, except that ferric nitrate is changed into bismuth nitrate, and the product is light yellow oily liquid with a yield of 62%. The NMR of this product is characterized as: 1 H NMR (500MHz, DMSO-d 6 )δ=4.26–4.16(m,2H),3.85–3.77(m,2H),3.77–3.73(m,2H),3.58–3.54(m,2H). 13 C NMR (126MHz, DMSO-d 6 ) δ=66.67, 65.18, 49.59, 40.30.

Embodiment 3

[0036] Synthesis of N-nitrosopiperidine

[0037]

[0038] The reaction steps are exactly the same as in Example 1, except that morpholine is changed to piperidine, and the reaction time is extended to 5h. The product is a light yellow oily liquid with a yield of 88%. The NMR of this product is characterized as: 1 H NMR (500MHz, Chloroform-d) δ=4.21–4.16(m,2H), 3.81–3.76(m,2H), 1.83–1.74(m,4H), 1.56(p,J=5.9,2H). 13 C NMR (126 MHz, Chloroform-d) δ = 51.04, 39.99, 26.59, 24.92, 24.32.

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Abstract

The invention discloses a synthesis method of a nitrosation product of secondary amine, which uses economic and nontoxic metal nitrate as a nitro source through electrocatalytic free radical couplingreaction to carry out non-oxidation N-nitrosation reaction on an N-H bond of morpholine, and the reaction system is suitable for various common secondary amines. According to the method, an electro-catalysis mode is adopted, various cheap metal nitrates are taken as nitrate sources, a target product is synthesized by adopting a one-step method, the reaction process is simple, the substrate universality is good, the yield of the generated nitrosamine compound is high, and a green N-N single bond construction method is realized.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry and relates to a synthesis method of nitrogen nitrosation products of secondary amines. Background technique [0002] As an important class of compounds, nitrogen-containing compounds have been widely used in pharmaceuticals, natural products and functional materials. Nitrification has a broad and varied significance. N-nitrosation of amines is an important and well-established reaction in organic reactions; nitrosation chemistry is a fruitful field for mechano-organic and biochemists. N-nitrosamines are a class of carcinogenic, mutagenic and teratogenic compounds. These compounds have biological significance and can be used as "trans-bactericides", ie NO-donor drugs. Therefore, seeking effective strategies to efficiently construct nitrogen-nitrogen bonds has been a major research topic in synthetic chemistry, among which, the introduction of nitroso and nitro radicals into the corres...

Claims

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Application Information

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IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 王鹏程赵季平陆明周新利
Owner NANJING UNIV OF SCI & TECH
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