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Prepn process of 2-[2-(2,2,2-trifluoro ethoxy)] phenoxy ethamine

A technology of trifluoroethoxy and phenoxyethylamine, which is applied in the field of preparation of 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine, achieving low price, The effect of high yield and mild reaction conditions

Inactive Publication Date: 2007-11-07
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine (I) (structural formula is as follows) is an important intermediate for the synthesis of Silodosin, and there is no bibliographical information about the synthesis of this intermediate

Method used

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  • Prepn process of 2-[2-(2,2,2-trifluoro ethoxy)] phenoxy ethamine
  • Prepn process of 2-[2-(2,2,2-trifluoro ethoxy)] phenoxy ethamine

Examples

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Embodiment 1

[0012] Embodiment 1, the preparation of 2-[2-(2,2,2-trifluoroethoxy)]phenoxybromoethane (III):

[0013] Add 36g of 2-(2,2,2-trifluoroethoxy)phenol (II), 40g of 1,2-dibromoethane, and 30g of 20% sodium hydroxide into the reaction flask, stir, heat, and reflux for 8 hours . Cooled to room temperature, the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give pale yellow oily substance 2-[2-(2,2,2-trifluoroethoxy)]phenoxybromoethane (III ) 48g, yield 85.6%.

Embodiment 2

[0014] Embodiment 2, the preparation of N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]phthalimide (IV):

[0015] Add 29g of 2-[2-(2,2,2-trifluoroethoxy)]phenoxybromoethane(III), 14.5g of phthalimide, 400ml of DMA into the reaction bottle, and stir the reaction at 50°C After 1 hour, 9 g of potassium hydroxide was added, and the mixture was refluxed for 1 hour. Cool to room temperature, add 600ml of water, filter with suction, wash with water, and dry to obtain white solid N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]phthaloyl Imine (IV) 30g, yield 84.7%, mp 120-122°C. MS (m / z): 365 (M + ).

Embodiment 3

[0016] Embodiment 3, the preparation of 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine (I):

[0017] Add N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]phthalimide (IV) 21g, absolute ethanol 300ml, 85 % Hydrazine Hydrate 3.0ml, heated and stirred under reflux for 1.5 hours, concentrated under reduced pressure, the residue was extracted with 50ml of chloroform × 2, washed with water, dried over anhydrous sodium sulfate, filtered, concentrated to give 12.5g of off-white solid, yield 92.4%, mp58~ 60°C. 1 HNMR (CDCl 3 )δ: 1.44 (brs, 2H, -NH 2 ), 3.10(t, 2H, -CH 2 NH 2 ), 4.04(t, 2H, -CH 2 OAr), 4.37(q,2H,-CH 2 CF 3 ), 6.89-7.26 (m, 4H, Ar-H). MS (m / z): 235 (M + ).

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PUM

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Abstract

The present invention relates to preparation process of 2-[2-(2, 2, 2-trifluoro ehtoxy)] phenoxy ethamine. The preparation process includes the etherification of 2-(2, 2, 2-trifluoro ehtoxy) phenol as material with 1, 2-dibromoethane to obtain 2-[2-(2, 2, 2-trifluoro ehtoxy)] phenoxy bromethane, the alkylation of 2-[2-(2, 2, 2-trifluoro ehtoxy)] phenoxy bromethane with phthalamide, and final aminolysis with hydrazine hydrate to obtain 2-[2-(2, 2, 2-trifluoro ehtoxy)] phenoxy ethamine.

Description

technical field [0001] The preparation method of 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine. Background technique [0002] The structural formula of Silodosin (KMD-3213, KAD-3213) is as follows, and it is jointly developed by Japanese Kissei and Daiichi companies α 1 - Adrenergic receptor antagonists, clinically used in the treatment of benign prostatic hyperplasia. This product was listed in Japan for the first time in 2006. For its synthesis, refer to EP600675. 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine (I) (structural formula is as follows) is an important compound for the synthesis of Silodosin Intermediate, there is no literature report on the synthesis of this intermediate. [0003] Contents of the invention [0004] The present invention is a new route and new method for preparing 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine (I). The present invention relates to the synthetic route of 2-[2-(2,2,2-trifluoroethoxy)]phenoxyethylamine (I) as follows: ...

Claims

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Application Information

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IPC IPC(8): C07C217/20C07C213/00
Inventor 陈国华罗小川陈颖黄文龙
Owner CHINA PHARM UNIV
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