Ethanamine, 2-[2-(2,2,2-trifluoroethoxy)phenoxy]-
2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethanamine
CAS: 751476-91-2
Molecular Formula: C10H12F3NO2
Ethanamine, 2-[2-(2,2,2-trifluoroethoxy)phenoxy]- - Names and Identifiers
Ethanamine, 2-[2-(2,2,2-trifluoroethoxy)phenoxy]- - Physico-chemical Properties
| Molecular Formula | C10H12F3NO2 |
| Molar Mass | 235.2 |
| Density | 1.234 |
| Melting Point | 58-60℃ |
| Boling Point | 264℃ |
| Flash Point | 114℃ |
| pKa | 8.50±0.10(Predicted) |
Ethanamine, 2-[2-(2,2,2-trifluoroethoxy)phenoxy]- - References
| Use | 2-[2-(2,2, 2-trifluoroethoxy) phenoxy] ethylamine is an intermediate in the synthesis of celodosin. Silodoxin (Silodosin, also known as Silodoxin). The chemical name of cylodoxin is: 2, 3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2, 2-trifluoroethoxy) phenoxy] ethylamine] propyl]-1H-indole-7-formamide. Xelodosin is an α1-receptor antagonist developed by the Japanese pharmaceutical company Kissei, which can be used to treat symptoms related to benign prostatic hyperplasia or hypertrophy. Japan's Orange Pharmaceutical Company applied for cooperation with the First Third Party (DaiichiSankyo) Pharmaceutical Company and was first approved for listing in Japan in May 2006 under the trade name Urief. Subsequently, Orange and the First Third Party also authorized Silodoxin to Watson Pharmaceutical Company, which was approved by the US Food and Drug Administration (FDA) in August 2008 and listed in the United States. The capsule preparation of Silodosin, imported by Japan's Daiichi Sankyo Pharmaceutical Company, was also listed in China in 2011. |
| Application | 2-[2-(2,2, 2-trifluoroethoxy) phenoxy] ethylamine can be used to prepare silodosin. 1-(3-hydroxypropyl) -7-cyano-5-(2-oxopropyl) indoline (II)(2.58g,10mmol), 2-[2-(2,2, 2-trifluoroethoxy) phenoxy] ethylamine (III)(2.58g,11mmol) and 1, 2-dichloroethane 35mL were added to the three-neck reaction bottle, sodium triacetoxyborohydride (3.0g,14mmol) and acetic acid (0.9g,15mmol) were added at room temperature and nitrogen atmosphere, the temperature was raised to 45-50 ℃, stirred for 20 hours, and TLC detection reaction was completed. Add 1N sodium hydroxide to quench the reaction, extract twice with 1, 2-dichloroethane, combine the organic phase, dry with anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain 2, 3-dihydro-1-(3-hydroxypropyl)-7-cyano -5-[2-[2-[2-(2,2,2-trifluoroethoxy) phenoxy] ethylaminoyl] propyl]-1H-indole (IV)4.1g, yield 86.0%. Add 2, 3-dihydro-1-(3-hydroxypropyl) -7-formamido-5-[2-[2-[2-(2,2, 2-trifluoroethoxy) phenoxy] ethylamino] propyl]-1H-indole (IV)(2.5g,5mmol) and methanol 40mL to the reaction bottle, S-( )-mandelic acid (0.8g,5mmol) is added under stirring, and placed in an ultrasonic generator and shaken for 30 minutes. The insoluble matter is filtered. The filter cake is washed with 10mL of ether and methanol mixture. The dried white solid is dissolved with 40mL of ethyl acetate and 40mL of 10% sodium hydroxide. After stirring at room temperature for 1 hour, the liquid is left standing and separated. The organic phase is dried with anhydrous magnesium sulfate and concentrated under reduced pressure, 0.88g of white solid silodoxin (I) was obtained with a yield of 35.2%. Compared with the existing technology, the synthesis method has the advantages of easy availability of raw materials, simple process, no protection of any functional groups, can effectively control costs and improve product quality, and promote the economic and technological development of the API. |
Last Update：2024-04-10 22:29:15
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Product Name: Silodosin Impurity 64 Visit Supplier Webpage Request for quotationCAS: 751476-91-2
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
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