52250-51-8

Usage

Uses

Used in Research Applications:
1-Phenyl-3,4-dihydroisochinoline hydrochloride is used as a research compound for its unique chemical properties and behavior in reactions with other chemicals. It aids in the study of biochemistry and medicinal chemistry, contributing to the understanding of complex chemical interactions and the development of new compounds.
Used in Synthesis of Complex Compounds:
1-Phenyl-3,4-dihydroisochinoline hydrochloride is used as a key intermediate in the synthesis of more complex compounds. Its structural formation and chemical attributes make it a valuable component in the creation of advanced chemical entities, which can be further utilized in various applications across different industries.
Used in Pharmaceutical Industry:
1-Phenyl-3,4-dihydroisochinoline hydrochloride is used as a building block in the development of pharmaceutical compounds. Its unique structure and reactivity with other chemicals allow for the creation of new drug candidates, which can be tested for potential therapeutic applications and contribute to the advancement of medicine.
Used in Chemical Industry:
1-Phenyl-3,4-dihydroisochinoline hydrochloride is used as a raw material in the production of various chemical products. Its versatility in reactions and compatibility with other compounds make it a valuable asset in the synthesis of a wide range of chemical products, from dyes to agrochemicals.

Upstream product

• 3278-14-6 N-phenethylbenzamide 
• 1422464-27-4 (S)-N-chloro-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 52095-42-8 phenyl(2-vinylphenyl)methanone 

Relevant academic research and scientific papers

One-pot racemization process of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline: A key intermediate for the antimuscarinic agent solifenacin

(S)-(+)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, which is the key intermediate in preparing the urinary antispasmodic drug solifenacin, was racemized in quantitative yield by a simple one-pot procedure through N-chlorination with trichloroisocyanuric acid, conversion of the N-chloroamine into the imine hydrochloride, and reduction of the imine double bond. The racemized amine was successfully resolved by d-(-)-tartaric acid obtaining (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in 81% yield and with 96.7% ee and, from the crystallization mother liquors, the R enriched form. This was racemized by the same one-pot process and resolved by d-(-)-tartaric acid with the same efficiency. Such an approach to the racemization of 1-phenyl-1,2,3,4- tetrahydroisoquinoline can be industrially useful to recycle the waste R enantiomer resulting from the classical resolution used to obtain the S enantiomer on a large scale.

The development of an asymmetric hydrogenation process for the preparation of solifenacin

The successful development of a catalytic imine asymmetric hydrogenation process for the reduction of the hydrochloride salt of 1-phenyl-3,4- dihydroisoquinoline to 1-(S)-phenyl-1,2,3,4-tetrahydroisoquinoline is described. This represents a novel approach to the key intermediate in preparing the urinary antispasmodic drug solifenacin, (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl-3, 4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate. Suitable reaction conditions were identified through an extensive screen of catalysts and combination of solvents and additives. The best reaction conditions: [Ir(COD)Cl] 2-(S)-P-Phos, molar substrate to catalyst ratio (S/C) of >1000/1, THF, 1-2 equiv of H3PO4, 60 °C, 20 bar H2, were reproduced on a 200 g scale (95% isolated yield, 98% ee and >99% HPLC product purity).