22940-59-6

Usage

InChI:InChI=1/C25H25NO3S/c1-20-12-14-23(15-13-20)30(28,29)26-18-16-25(17-19-26,22-10-6-3-7-11-22)24(27)21-8-4-2-5-9-21/h2-15H,16-19H2,1H3

Upstream product

• 108-86-1 bromobenzene 
• 24476-55-9 N-(p-tosyl)-4-phenyl-4-cyano-piperidine 
• 1127547-60-7 C₂₅H₂₇NO₃S 
• 98-59-9 p-toluenesulfonyl chloride 
• 37586-22-4 4-benzoylpiperidine 
• 852860-46-9 diphenyl[1-(toluene-4-sulfonyl)piperidin-4-yl]methanol 
• 922504-26-5 phenyl(1-tosylpiperidin-4-yl)methanone 
• 916976-33-5 4-benzhydrylidene-1-(4-methylphenylsulfonyl)-piperidine 

Downstream Products

• 22940-60-9 4-benzoyl-4-phenylpiperidne 

Relevant academic research and scientific papers

Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter

To identify selective high-affinity inhibitors of the vesicular acetylcholine transporter (VAChT), we have interposed a carbonyl group between the phenyl and piperidyl groups of the prototypical VAChT ligand vesamicol and its more potent analogues benzovesamicol and 5-aminobenzovesamicol. Of 33 compounds synthesized and tested, 6 display very high affinity for VAChT (K i, 0.25-0.66 nM) and greater than 500-fold selectivity for VAChT over σ1 and σ2 receptors. Twelve compounds have high affinity (Ki, 1.0-10 nM) and good selectivity for VAChT. Furthermore, 3 halogenated compounds, namely, trans-3-[4-(4-fluorobenzoyl) piperidinyl]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (28b) (Ki = 2.7 nM, VAChT/sigma selectivity index = 70), trans-3-[4-(5-iodothienylcarbonyl) piperidinyl]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (28h) (Ki = 0.66 nM, VAChT/sigma selectivity index = 294), and 5-amino-3-[4-(p-fluorobenzoyl) piperidinyl]-2-hydroxy-1,2,3,4,-tetrahydronaphthalene (30b) (Ki = 2.40 nM, VAChT/sigma selectivity index = 410) display moderate to high selectivity for VAChT. These three compounds can be synthesized with the corresponding radioisotopes so as to serve as PET/SPECT probes for imaging the VAChT in vivo.

BF3-OEt2-mediated rearrangement of (4-phenylpiperidin-4-yl)-arylmethanols

Synthesis of several 4-benzhydrylidenepiperidine analogs has been established starting from different (4-phenylpiperidin-4-yl)-arylmethanols via boron trifluoride etherate mediated rearrangement. The possible rearranged mechanism was proposed. Boron trifluoride etherate-mediated rearrangement of the related derivatives was also examined. It presents a novel rearrangement reaction catalyzed by boron trifluoride etherate and broadens the scope of application.

CAN-mediated rearrangement of 4-benzhydrylidenepiperidines

Several 1-substituted phenyl-(4-phenylpiperidin-4-yl)methanones are synthesized in modest overall yields starting from the reaction of different 1-substituted 4-benzhydrylidenepiperidines via CAN-mediated rearrangement. This facile strategy was also used to synthesize meperidine analog.