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Pharmaceutical synthesis of 4-methoxy-alpha-methyl-phenethylamine

A synthetic method and methoxy technology, applied in chemical instruments and methods, preparation of amino hydroxyl compounds, organic chemistry, etc., can solve the problems of low yield, high equipment requirements, long reaction time, etc., and achieve high reaction yield, The effect of good product purity and shortened reaction time

Inactive Publication Date: 2007-04-04
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. The use of high-pressure hydrogenation kettle requires high equipment requirements
[0007] 2. Long reaction time, complete reaction within 48 hours
[0008] Low yield, only 62-68%

Method used

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  • Pharmaceutical synthesis of 4-methoxy-alpha-methyl-phenethylamine
  • Pharmaceutical synthesis of 4-methoxy-alpha-methyl-phenethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (R, R)-4-methoxy-α-methyl-N-(1-phenyl)-phenethylamine hydrochloride 30g and ammonium formate 12.4g and 10% palladium carbon hydrogenation catalyst 3g, Add 500ml of methanol, heat to reflux for 3 hours, filter the catalyst after cooling, collect the target product R-4-methoxy-α-methyl-phenethylamine hydrochloride 18.4g after recovering the solvent, the yield is 93%. 1 HNMR (CDCl 3 )δ: 1.29(d,3H,-CH 3 ), 2.58~2.75 (m, 2H, -CH 2- ), 3.16 (m, 1H, -CH-), 3.79 (S, 3H, -OCH 3 ), 6.84 (d, 2H), 7.14 (d, 2H); EI-MS (m / z): 166 [(M+H), 100], 149 (48); elemental analysis (C 10 h 16 ClNO) measured value (calculated value, %): C59.46 (59.55), H7.72 (7.80), N6.84 (6.95); [α] D 25 =-22.5°C (C=2, H 2 O); mp: 250-251°C.

Embodiment 2

[0031] (S, S)-4-methoxy-α-methyl-N-(1-phenyl)-phenethylamine hydrobromide 30g and ammonium formate 27.1g and 10% palladium carbon hydrogenation catalyst 1.5 g, add 500ml of ethanol, heat and reflux for 4 hours, filter the catalyst after cooling, collect the target product S-4-methoxy-α-methyl-phenylethylamine hydrobromide 19.2g after recovering the solvent, the yield is 91% . Elemental analysis (C 10 h 16 BrNO) measured value (calculated value, %): C48.65 (48.79), H6.52 (6.55), N5.64 (5.69).

Embodiment 3

[0033] (R, S)-4-methoxy-α-methyl-N-(1-phenyl)-phenethylamine hydrochloride 3g and ammonium formate 6.2g and 5% palladium carbon hydrogenation catalyst 0.6g , add 50ml tetrahydrofuran, heat to reflux for 3 hours, filter the catalyst after cooling, collect the target product R-4-methoxy-α-methyl-phenethylamine hydrochloride 1.78g after recovering the solvent, the yield is 90%.

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PUM

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Abstract

Synthesis of accepted salt tazolol hydrochloride critical intermediate 4-methoxyl-alpha-methyl-phenethyl amine is carried out by debenzyl reacting accepted salt 4-methoxyl-alpha-methyl-N-(1-benzyl)-phenethyl amine with ammonium formate under existence of palladium carbon hydrogenation catalyst to obtain the final product. It has shorter reactive time, more yield and is cheap.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing a pharmaceutically acceptable salt of tamsulosin hydrochloride key intermediate 4-methoxy-α-methyl-phenethylamine for treating benign prostatic hyperplasia. Background technique [0002] Tamsulosin hydrochloride is a long-acting α1A adrenergic receptor blocker for benign prostatic hyperplasia, developed by Japan’s Yamanouchi Pharmaceutical Co., Ltd., first listed in Japan in 1993, and successively transferred to Abbott (Flomax) and Boehringer Ingelheim (Boehringer Ingelheim, trade name Flomax) and 65 countries around the world. It was put into the Chinese market in 1996 under the trade name of Harnal. The product has shown a strong momentum of development after it was launched in my country, and its market share has been rising steadily, and it has entered the national essential drug list. The drug specifically inhibits the contraction of the smooth ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/60C07C213/08
Inventor 张福利胡猛谢美华
Owner SHANGHAI INST OF PHARMA IND CO LTD
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