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Production method of optically active N-benzyl-1-phenylethylamine

A technology of benzylphenethylamine and optical activity, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems affecting product quality and yield, inconvenient operation, cumbersome steps, etc., to reduce difficulty and Effects of workload, improvement of quality and yield, and reduction of production cost

Inactive Publication Date: 2009-09-09
SHANDONG YUEXING CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many process routes and cumbersome steps, which not only bring inconvenience to the operation, but also affect the quality and yield of the product, and even cause racemization of the product, and cause many "three wastes" and serious environmental pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0026] Drop into 121g R-(+)-a-phenethylamine in 500mL autoclave And 106g benzaldehyde and 1.5g above-mentioned palladium charcoal, use N 2 Replace the air as a protective atmosphere, stir and raise the temperature to 60°C and start the hydrogen reaction for 4 hours until no hydrogen is absorbed. At this time, the reaction temperature is 95°C and the pressure is 4.5MPa. distilled.

[0027] After 26 mL of dehydration under normal pressure, 8.0 g of the fore distillation was collected under reduced pressure, and 192 g of the finished product N-benzyl-phenethylamine was collected. Finished product N-benzyl-phenethylamine assay result: purity Gc 99.75%, Mass yield: 159%; Molar yield: 91% (calculated as phenylethylamine)

Embodiment approach 2

[0029] Drop into 121g S (-)-phenethylamine in 500mL autoclave, and 103g of benzaldehyde and 0.5g of palladium carbon, replace the air with nitrogen, stir and raise the temperature to 65°C and start to flow hydrogen. After 230 minutes of reaction, there is basically no absorption. At this time, the reaction temperature is 100°C, the pressure is 5.1MPa, and the heat preservation is continued for half an hour. , maintain warm discharge, filter the catalyst for distillation.

[0030] After dehydrating 25.5 mL under normal pressure, 6.5 g of the fore distillation was collected under reduced pressure, and 194 g of the finished product N-benzyl-phenethylamine was collected. Its molar yield is 92%; mass yield is 160.3% (in terms of phenethylamine); N-benzyl-phenethylamine purity Gc is 99.73%,

Embodiment approach 3

[0032] Drop into 121g R(+)-phenethylamine in 500mL autoclave With 108g of benzaldehyde and 1.1g of self-made palladium charcoal, replace the air with nitrogen, stir and raise the temperature to 70°C and start to flow hydrogen. After 248 minutes of reaction, no hydrogen is absorbed. At this time, the reaction temperature is 104°C and the pressure is 5.4MPa. After 35 minutes, the material was discharged, and the catalyst was filtered to carry out distillation. After dehydrating 25.5ml under normal pressure, 10.5g of fore distillation was collected under reduced pressure, and 190g of finished product N-benzyl-phenethylamine was collected. Its molar yield is 90%; mass yield is 157% (in terms of phenethylamine); assay results: purity Gc 99.73%,

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Abstract

The invention relates to a production method of optically active N-benzyl-1-phenylethylamine, in particular to the production of optically active N-benzyl-1-phenylethylamine in the field of chemical industry. Optically active phenylethylamine and benzaldehyde as well as a palladium-charcoal as a catalyst are respectively put into a pressure kettle and replaced by N2 thrice, hydrogen gas is introduced into the pressure kettle when the reactants are stirred and heated until no hydrogen is absorbed in the reaction, the reaction is kept for half an hour under the conditions of heat preservation and pressure maintaining, the mixture is discharged after being cooled and the palladium-charcoal as a catalyst is filtered out; the reaction products with the catalyst being filtered out is dehydrated through atmospheric distillation, then a small amount of front cut fractions are removed through reduced pressure distillation and 169 DEG C to 173 DEG C / 15mmHg of fractions, namely the finished products are collected. Not only higher optical activity of the optically active N-benzyl-1-phenylethylamine produced by the method can be obtained, but also the yield can be stabilized at 90 percent to 93 percent and the chemical purity can reach more than 99.8 percent.

Description

technical field [0001] The invention relates to the production of N-benzylphenethylamine in the field of chemical industry, in particular to a production method of optically active N-benzylphenethylamine. Background technique [0002] With the updating and development of science and technology, the field of organic synthesis is also changing with each passing day. At the same time, due to the needs of the development and synthesis of some new drugs, the synthetic and optically active products are more and more valued and favored by people. [0003] The optically active N-benzyl-phenethylamine is a highly stereoselective, widely used resolving agent and catalyst ligand for asymmetric reactions. For example, using optically active N-benzyl-phenylethylamine as a resolving agent can well resolve the new drug clapidol precursor o-chloromandelic acid, the precursor β-hydroxycarboxylic acid of HIV protease inhibitors; using optically active N -Benzylphenethylamine as a ligand can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/27C07C209/78C07B53/00B01J23/44
Inventor 瞿国生瞿春生瞿益栋赵家明孙剑
Owner SHANDONG YUEXING CHEM CO LTD
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