ChemicalBook CAS DataBase List 1-(6-nitropyridin-3-yl)piperazine

1-(6-nitropyridin-3-yl)piperazine synthesis

4synthesis methods

Product Name:1-(6-nitropyridin-3-yl)piperazine
CAS Number:775288-71-6
Molecular formula:C9H12N4O2
Molecular Weight:208.22

110-85-0 Synthesis

110-85-0
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$5.00/5 g

39856-50-3 Synthesis

39856-50-3
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$6.00/5g

775288-71-6
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Yield: 94.8%

Reaction Conditions:

with modified hectorite-loaded ionic liquid in dimethyl sulfoxide at 80; for 5 h;Green chemistry;Solvent;Reagent/catalyst;

Steps:

4 Example 4
1) 5-Bromo-2-nitropyridine (1 mol, 203 g) was dissolved in 1.5 L of dimethyl sulfoxide, and then an organically modified hectorite-supported ionic liquid material MHIL (40.6 g, 20 wt%) was added. Agitating and dispersing uniformly to obtain a first mixed liquid;2) Piperazine (129.2 g, 1.5 mol) was dissolved in 800 ml of dimethyl sulfoxide to form a piperazine solution, and then the piperazine solution was added dropwise to the first mixture to carry out a condensation reaction at 80 ° C;3) After 5 hours, the reaction solution was taken for HPLC detection (the percentage of 5-bromo-2-nitropyridine in the reaction solution was 0.08%, and the target product 1-(6-nitropyridin-3-yl)piperazine was 99.68%. Double condensation by-product 0.17%, the balance is unknown impurities), stop the reaction, use an organic microporous membrane with a pore size of 0.5 μm to filter and remove the organic modified hectorite-loaded ionic liquid material to obtain a filtrate;4) The filtrate is warmed to 60-65 ° C, and then the aqueous solution of methylamine at a concentration of 3 V% is added dropwise. When the turbidity occurs in the system, the dropwise addition is stopped, the mixture is kept warm for 20-30 min, and then the aqueous solution of methylamine having a concentration of 3 V% is continuously added dropwise. The concentration of 1-(6-nitropyridin-3-yl)piperazine in the solution was no longer decreased, and the temperature was naturally lowered to room temperature, filtered, and dried under vacuum at 45 ° C to obtain 197.4 g of a solid. The yield was 94.8%. 99.92% (external standard method); LC-MS: m/z = 209.1 [M+H].The ionic liquid material supported by the organic modified hectorite filtered by filtration was air-dried by acetone and recovered, and the yield of 1-(6-nitropyridin-3-yl)piperazine was 94.2%, and the content was 99.89%. Compared with the catalytic effect of fresh preparation, the catalytic material prepared by the invention can be recycled and used to reduce the production cost of the condensation step.

References:

Zheng Chuanhua;Lu Xueling;Zhang Lei CN109369517, 2019, A Location in patent:Paragraph 0053; 0060; 0064-0069

571189-16-7 Synthesis