Purifying method of (r)-n-(3,4-dimethoxy benzyl)-1-phenylethylamine l-tartrate and purifying method of (r)-n-(3,4-dimethoxy benzyl)-1-phenylethylamine

A technology of dimethoxybenzyl and phenylethylamine, which is applied in organic chemical methods, chemical instruments and methods, purification/separation/stabilization of organic compounds, etc., and can solve problems such as purity reduction

Inactive Publication Date: 2006-08-23
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine is a liquid with a high boiling point. In the mass production of the factory, due to the activity of the catalyst or the reaction temperature, In the case of decomposition products due to changes in hydrogen pressure, etc., or when the purity is reduced due to the mixing of impurities in optical resolution, there is no known economical purification method. In short, it is hoped that it will appear in the industry. Purification method that is also advantageous

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0039] At 43-48°C, add veratraldehyde (1658 parts by weight) and triethylamine (48 parts by weight) to isopropanol (3104 parts by volume), and add (R) dropwise for 1.6 hours at about 50°C -1-Phenylethylamine (1151 parts by weight), followed by stirring at the same temperature for 1 hour. Add 5% palladium-on-carbon (50% wet, 25.6 parts by weight) and isopropanol (1103 parts by volume) to the solution, and stir for 6.75 hours at 44-49° C. and 0.024-0.405 MPa hydrogen atmosphere. After filtering the catalyst, the filtrate was concentrated to obtain the amine compound.

[0040] IR(vcm -1 ) 3325(N-H), 1514(N-H).

Embodiment 1

[0042] 14.2 g (13.57 g in terms of 100% purity, 50 mmol) of this amine compound having an optical purity of 94.04% ee was dissolved in 210 g of acetone. At 40°C, 15.0 g (50 mmol) of 50% L-tartaric acid aqueous solution was added dropwise, followed by cooling to 21°C. The crystals were filtered to obtain 20.44 g of white crystals.

[0043] The optical purity of this amine compound was measured by HPLC and found to be 98.3% ee.

[0044] 1 H-NMR (DMSO-d 6 )1.45 (3H, d, J=6.8Hz, NHCHCH 3 ), 3.65 (1H, d, J=13.2Hz, NHCH 2 Ar), 3.74-3.76 (1H, m, NHCH 2Ar), 3.74 (6H, s, OCH 3 ), 4.00-4.10 (1H, m, NHCHCH 3 ), 4.07 (2H, s, HOCHCO 2 H), 6.84 (1H, d, J=8Hz, Ar-H of dimethoxyphenyl), 6.92 (1H, d, J=8Hz, Ar-H of dimethoxyphenyl), 6.99 (1H , s, Ar-H of dimethoxyphenyl), 7.34-7.47 (5H, m, C 6 h 5 ).

[0045] IR(KBr)3321.9, 2976.0, 1605.0, 1521.3, 1266.1cm -1

Embodiment 2

[0047] 14.2 g (13.57 g in terms of 100% purity) of this amine compound having an optical purity of 94.04% ee was dissolved in 210 g of acetone. At 50°C, 15.0 g of 50% L-tartaric acid aqueous solution was added dropwise, and then cooled to 25°C. The crystals were filtered to obtain 20.99 g of white crystals.

[0048] The obtained crystals were suspended in 60 ml of toluene and 25 ml of water, 20 g of a 20% aqueous solution of caustic soda was added and stirred, and the organic layer was separated. The obtained organic layer was washed with water and then concentrated to obtain 12.60 g of the amine compound (yield: 93%).

[0049] The optical purity was determined by HPLC and found to be 99.39% ee.

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PUM

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Abstract

The invention provided a method of industrially simply purifying (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine whose purity is reduced by mixing decomposed products and impurities thereinto. (R)-N-(3,4-Dimethoxybenzyl)-1-phenylethylamine L-tartrate is provided. The method of purifying (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine comprises adding L-tartaric acid to the (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine of reduced purity to obtain (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine L-tartrate of high purity as a crystal.

Description

technical field [0001] The present invention relates to the L-tartrate and (R)-N-(3, Purification method of 4-dimethoxybenzyl)-1-phenylethylamine. Background technique [0002] (R)-N-(3,4-Dimethoxybenzyl)-1-phenylethylamine is known as a useful optical resolving agent (eg WO03 / 066564A1). However, (R)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine is a liquid with a high boiling point. In the mass production of the factory, due to the activity of the catalyst or the reaction temperature, In the case of decomposition products due to changes in hydrogen pressure, etc., or when the purity is reduced due to the mixing of impurities in optical resolution, there is no known economical purification method. In short, it is hoped that it will appear in the industry. Also advantageous purification methods. Contents of the invention [0003] An object of the present invention is to provide a simple and industrially advantageous method for purifying (R)-N-(3,4-dimethoxybenzyl)-1-phenyle...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B63/00C07C217/58C07C217/68
Inventor 桂正板谷信重田中正英
Owner SUMITOMO CHEM CO LTD
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