221109-25-7

Basic information

• Product Name: 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• Synonyms: 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• CAS NO: 221109-25-7
• Molecular Weight: 274.365
• Mol File: 221109-25-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole(221109-25-7)
• EPA Substance Registry System: 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole(221109-25-7)

Safety Data

• Hazardous Substances Data: 221109-25-7(Hazardous Substances Data)

Upstream product

• 948-65-2 2-phenyl-indole 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 41661-47-6 piperidin-4-one 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 221109-26-8 3-(Piperidin-4-yl)-2-phenyl-1H-indole 
• 297165-79-8 (3S,4S)-3-(4-fluoro-piperidin-3-yl)-2-phenyl-1H-indole 
• 244087-35-2 4-(2-phenyl-1H-indol-3-yl)-2,3-dihydro-6H-pyridine-1-carboxylic acid benzyl ester 

Relevant articles and documents

3-(4-piperidinyl)- and 3-(8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-1H-indoles as bioavailable h5-HT(2A) antagonists

A series of 3-(4-piperidinyl)- and 3-(8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-1H-indoles have been prepared and evaluated as ligands for the h5-HT(2A) receptor. 3-(8-Phenethyl-8-aza-bicyclo[3.2.1]oct-3-yI)-2-phenyl-1H-indole is a high-affinity (1.2nM), selective (>800 fold over h5-HT(2C) and hD2 receptors) antagonist at the h5-HT(2A) receptor with oral bioavailability in rats. (C) 2000 Elsevier Science Ltd.

Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction

A rearrangement reaction involving the indole nucleus was investigated using stereochemical markers and low-temperature NMR experiments. Treatment of(3S,4S)-3-hydroxy-4-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with diethylaminosulfur trifluoride gave stereospecifically (3S,4S)-4-fluoro-3-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with complete regioselectivity. The initial formation of a reactive spirocyclopropyl-3H-indole intermediate is believed to be responsible for the stereo- and regiochemical outcome of the reaction.