A kind of preparation method of (±)‑1,2‑diphenylethylenediamine

A technology for diphenylethylenediamine and diphenylethylenedione dioxime, which is applied in the field of preparation of -1,2-diphenylethylenediamine, can solve problems such as difficulties in industrialization, and achieves environmental friendliness and ease of use. Industrial production conditions and the effect of less by-products

Active Publication Date: 2017-05-17
LIANYUNGANG CHIRAL CHEM CHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The methods reported in Document 3 (Can.J.Research.1934, 11:628~636.); Document 4 (IndianJ.Chem., 1980, 19B:73.) all use metal sodium reduction, which has high potential safety hazards and is difficult to industrialize

Method used

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  • A kind of preparation method of (±)‑1,2‑diphenylethylenediamine
  • A kind of preparation method of (±)‑1,2‑diphenylethylenediamine
  • A kind of preparation method of (±)‑1,2‑diphenylethylenediamine

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Effect test

Embodiment 1

[0032] Add 1,2-diphenylethanedionedioxime (48g, 0.20mol) and 260ml of methanol into a 500ml four-necked flask equipped with a condenser, stir to dissolve them all, then add 2g of activated carbon (120 mesh), 0.5 g Raney nickel, heat up to 60°C, slowly add 80% hydrazine hydrate (28.75g, 0.46mol) dropwise, keep the reaction temperature between 58°C-62°C, nitrogen will be released during the reaction, and the dropping rate should be controlled under nitrogen The release rate should not be too fast, and the liquid chromatography should track the reaction process. When the raw material 1,2-diphenylethylenedionedioxime disappears, the reaction is completed, the mixed solution is cooled, Raney nickel and activated carbon are filtered, and a small amount of water is covered for storage. For further use, the filtrate was distilled to recover methanol, the residue was added to 200ml of petroleum ether and heated to dissolve it, cooled for 24 hours and filtered to obtain 41.55g of (±)-1,2...

Embodiment 2

[0036] Add 1,2-diphenylethanedione dioxime (48g, 0.20mol) and 300ml ethanol into a 500ml four-necked flask equipped with a condenser, stir to dissolve them all, then add 2g of activated carbon (120 mesh), 0.5 g Raney nickel, heat up to 60°C, slowly add 80% hydrazine hydrate (28.75g, 0.46mol) dropwise, keep the reaction temperature between 58°C-62°C, nitrogen will be released during the reaction, and the dropping rate should be controlled under nitrogen The release rate should not be too fast, and the liquid chromatography should track the reaction process. When the raw material 1,2-diphenylethylenedionedioxime disappears, the reaction is completed, the mixed solution is cooled, Raney nickel and activated carbon are filtered, and a small amount of water is covered for storage. For further use, the filtrate was distilled to recover ethanol, the residue was added to 200ml of petroleum ether and heated to dissolve it, cooled for 24 hours and filtered to obtain 41.13g of (±)-1,2-dip...

Embodiment 3

[0040] Add 1,2-diphenylethanedione dioxime (48g, 0.20mol) and 300ml methanol into a 500ml four-necked flask equipped with a condenser, stir to make it all dissolve, then add 2g of activated carbon (120 mesh), 1.9 g cobalt chloride, heat up to 60°C, slowly add 50% hydrazine hydrate (46g, 0.46mol) dropwise, keep the reaction temperature between 60°C-62°C, nitrogen will be released during the reaction, and the dropping rate will be controlled at the nitrogen release The speed should not be too fast, and the liquid chromatography should track the reaction process. When the raw material 1,2-diphenylethylenedionedioxime disappears, the reaction is completed, the mixed solution is cooled, Raney nickel and activated carbon are filtered, and a small amount of water is covered to preserve it. For further use, the filtrate was distilled to recover methanol, the residue was added to 200ml of petroleum ether and heated to dissolve it, cooled for 24 hours and filtered to obtain 36.46g of (±)...

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Abstract

The invention discloses a preparation method for (+ / -)-1,2-diphenylethanediamine. The (+ / -)-1,2-diphenylethanediamine in the invention is prepared from 1,2-dibenzoyl dioxime by catalytic reduction in a polar solvent at 20 DEG C to 100 DEG C with one selected from the system consisting of hydrazine hydrate, formic acid, sodium formate, ammonium formate, and ammonium formate-triethylamine as a hydrogen source, and with raney nickel as a catalyst and activated carbon as a cocatalyst. The preparation method provided by the invention has the advantages of simple and wide raw material sources, low price, safe production process, short process flow, mild reaction conditions, low cost, environment friendliness, etc., and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of (±)-1,2-diphenylethylenediamine, which belongs to the field of organic synthesis. Background technique [0002] (±)-1,2-Diphenylethylenediamine was prepared by resolution of (1R,2R)-(+)-1,2-diphenylethylenediamine and (1S,2S)-(-)-1 ,The racemate of 2-diphenylethylenediamine chiral ligand, chiral (±)-1,2-diphenylethylenediamine in chiral drugs, chiral pesticides, chiral liquid crystals, chiral spices etc. have broad application prospects. [0003] Document 1 (Chinese Journal of Pharmaceutical Industry, 1993, 24(6): 2802281) reported an improvement in the synthesis and resolution of (±)-1,2-diphenylethylenediamine. This method uses benzaldehyde and liquid ammonia to react through cyclization and rearrangement to obtain 2,4,5-triphenylimidazoline, and then obtain the product through acetylation and hydrolysis. In the method, such as the acetylation product: (±) -N-acetyl-N'-benzoyl-1,2-phenylethylenediam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/40C07C211/27
Inventor 沈国胜
Owner LIANYUNGANG CHIRAL CHEM CHINA CO LTD
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