The Synthetic Routes of Silodosin

Synthetic routes of silodosin are various methods that are used to synthesize this compound in the chemical industry.
Silodosin is a phosphodiesterase type 5 inhibitor that is used to treat benign prostatic hyperplasia and is sold under the brand name Rapaflo.
The following are some of the commonly used synthetic routes for silodosin.

1. Hydrochlorination of N-[2,6-dichlorophenyl]-5-ethyl-2,3-dihydro-1H-inden-1-amine

This route involves the hydrochlorination of N-[2,6-dichlorophenyl]-5-ethyl-2,3-dihydro-1H-inden-1-amine to produce silodosin.
The hydrochlorination reaction is carried out in the presence of a solvent such as THF or DMF and a catalyst such as hydrogen chloride gas.
The reaction is typically carried out at a temperature of approximately 50-70°C.

2. Nitrating of N-[2-chloro-5-[(dibenzylamino)oxy]phenyl]-2,3-dihydro-1H-inden-1-amine

This route involves the nitrating of N-[2-chloro-5-[(dibenzylamino)oxy]phenyl]-2,3-dihydro-1H-inden-1-amine to produce silodosin.
The nitrating reaction is carried out in the presence of a solvent such as DMF and a catalyst such as nitric acid.
The reaction is typically carried out at a temperature of approximately 50-70°C.

3. Chlorination of 5-ethyl-2,3-dihydro-1H-inden-1-amine

This route involves the chlorination of 5-ethyl-2,3-dihydro-1H-inden-1-amine to produce silodosin.
The chlorination reaction is carried out in the presence of a solvent such as CHCl3 and a catalyst such as bleach (NaOCl).
The reaction is typically carried out at a temperature of approximately 0-10°C.

4. Reduction of 2-chloro-5-[(dibenzylamino) oxy]benzaldehyde

This route involves the reduction of 2-chloro-5-[(dibenzylamino) oxy]benzaldehyde to produce silodosin.
The reduction reaction is carried out in the presence of a reducing agent such as lithium aluminum hydride (LiAlH4) and a solvent such as THF.
The reaction is typically carried out at a temperature of approximately 50-70°C.

In conclusion, the synthetic routes of silodosin involve various methods that are used to synthesize this compound in the chemical industry.
These routes include hydrochlorination of N-[2,6-dichlorophenyl]-5-ethyl-2,3-dihydro-1H-inden-1-amine, nitrating of N-[2-chloro-5-[(dibenzylamino)oxy]phenyl]-2,3-dihydro-1H-inden-1-amine, chlorination of 5-ethyl-2,3-dihydro-1H-inden-1-amine, and reduction of 2-chloro-5-[(dibenzylamino) oxy]benzaldehyde.
The selection of the synthetic route depends on the availability of the starting materials and the desired yield of the product.