306296-91-3

Basic information

• Product Name: Piperazine, 2-methyl-4-(4-piperidinyl)-1-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]-, (2S)-
• CAS NO: 306296-91-3
• Molecular Formula: C19H28F3N3
• Molecular Weight: 355.447
• Mol File: 306296-91-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Piperazine, 2-methyl-4-(4-piperidinyl)-1-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 2-methyl-4-(4-piperidinyl)-1-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]-, (2S)-(306296-91-3)
• EPA Substance Registry System: Piperazine, 2-methyl-4-(4-piperidinyl)-1-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]-, (2S)-(306296-91-3)

Safety Data

• Hazardous Substances Data: 306296-91-3(Hazardous Substances Data)

Upstream product

• 741687-11-6 (2S)-2-{(2-chloroacetyl)[(1S)-1-(4-trifluoromethylphenyl)ethyl]amino}propionic acid methyl ester 
• 741687-10-5 (2S)-2-[(1S)-1-(4-trifluoromethylphenyl)ethylamino]propionic acid methyl ester 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 845834-58-4 4-{3-methyl-2,5-dioxo-4-[1-(4-trifluoromethylphenyl)ethyl]piperazin-1-yl}piperidine-1-carboxylic acid tert-butyl ester 
• 1737-26-4 1-(4-trifluorophenyl)ethanol 

Relevant articles and documents

Forward- and reverse-synthesis of piperazinopiperidine amide analogs: A general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists

Piperazinopiperidine amide analogs are among the most promising CCR5 antagonists. As an effective extension of a previously-reported methodology to synthesize such compounds, forward- and reverse-syntheses were successfully developed in which the convergent synthesis of the piperazinopiperidine nucleus, with a building block of 4-substituent-4-aminopiperidine, served as a common key step. The two-way approach affords a comprehensive access to the piperazinopiperidine templated library with variation on the pharmacophore sites. Thus, a SAR study of our synthesized piperazinopiperidine-based CCR5 antagonists was conducted with respect to the structure and configuration of the substituent on the piperazine ring. The S-configuration of the benzylic-substituent is vital for the CCR5 binding, and the bulky or aryl substituent on the 2-position in the piperazine ring is detrimental to the activity. By using the forward-synthesis approach, the best compound in the chiral piperazine-based CCR5 antagonist series, Sch-D (Vicriviroc), was conveniently synthesized in an excellent yield. The Royal Society of Chemistry.

An improved synthesis of piperazino-piperidine based CCR5 antagonists with flexible variation on pharmacophore sites

An improved and efficient synthetic route towards piperidino-piperazine based CCR5 antagonists was developed. The new approach was flexible for introducing various substituents in the pharmacophore sites via Grignard reagent addition and reductive amination. l-Amino acids were used as a chiral pool to introduce and then induce the desired stereochemistries, meanwhile rendering the variable substitution. The efficient construction of the piperazino-piperidine nucleus was achieved in a highly convergent manner with a key building block of N1-Boc-4-substituent-4-aminopiperidine, exhibiting significant advantages in terms of concise synthetic route and environmental-friendly reagents over the previously described stepwise synthesis, in which a modified Strecker reaction was involved with highly toxic reagents such as diethylaluminum cyanide.