63959-33-1

Basic information

• Product Name: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile
• Synonyms: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile;4-(4-Chlorophenyl)-4-hydroxy-α,α-diphenyl-;4-(4-Chlorophenyl)-4-hydroxy-alpha,alpha-diphenyl-1-piperidinebutanenitrile;4-(4-Chlorophenyl)-4-hydroxy-α,α-diphenyl-1-piperidinebutanenitrile
• CAS NO: 63959-33-1
• Molecular Formula: C₂₇H₂₇ClN₂O
• Molecular Weight: 430.96908
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 63959-33-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 626.907°C at 760 mmHg
• Flash Point: 332.942°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile(63959-33-1)
• EPA Substance Registry System: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile(63959-33-1)

Safety Data

• Hazardous Substances Data: 63959-33-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An intermediate for the synthesis of opioid-receptor agonists

InChI:InChI=1/C27H27ClN2O/c28-25-13-11-24(12-14-25)27(31)16-19-30(20-17-27)18-15-26(21-29,22-7-3-1-4-8-22)23-9-5-2-6-10-23/h1-14,31H,15-20H2

Upstream product

• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 39186-58-8 4-bromo-2,2-diphenylbutyronitrile 
• 60-29-7 diethyl ether 

Downstream Products

• 66164-06-5 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-2,2-diphenylbutanamide 
• 1424272-65-0 4-(4-(4-chlorophenyl)-4-hydroxypiperidine-1-yl)-N-(3-fluoropropyl)-2,2-diphenylbutanamide 
• 1424272-64-9 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N-(2-fluoroethyl)-2,2-diphenylbutanamide 
• 1424272-68-3 [N-ethyl-¹⁸F]-N-desmethylloperamide 
• 1424272-67-2 11-(4-chlorophenyl)-4,4-diphenyl-10-oxa-1,6-diazabicyclo[9.2.2]pentadecan-5-one 

Relevant articles and documents

Identification of novel small-molecule inhibitors targeting menin-MLL interaction, repurposing the antidiarrheal loperamide

Leukemia with a mixed lineage leukemia (MLL) rearrangement, which harbors a variety of MLL fusion proteins, has a poor prognosis despite the latest improved treatment options. Menin has been reported to be a required cofactor for the leukemogenic activity of MLL fusion proteins. Thus, the disruption of the protein-protein interactions between menin and MLL represents a very promising strategy for curing MLL leukemia. Making use of menin-MLL inhibitors with a shape-based scaffold hopping approach, we have discovered that the antidiarrheal loperamide displays previously unreported mild inhibition for the menin-MLL interaction (IC50 = 69 ± 3 μM). In an effort to repurpose this drug, a series of chemical modification analyses was performed, and three of the loperamide-based analogues, DC-YM21, DC-YM25 and DC-YM26 displayed better activities with IC50 values of 0.83 ± 0.13 μM, 0.69 ± 0.07 μM and 0.66 ± 0.05 μM, respectively. Further treatment with DC-YM21 demonstrated potent and selective blockage of proliferation and induction of both cell cycle arrest and differentiation of leukemia cells harboring MLL translocations, which confirmed the specific mechanism of action. In conclusion, molecules of a novel scaffold targeting menin-MLL interactions were reported and they may serve as new potential therapeutic agents for MLL leukemia.

A high-yield route to synthesize the P-glycoprotein radioligand [ 11C]N-desmethyl-loperamide and its parent radioligand [ 11C]loperamide

N-Desmethyl-loperamide and loperamide were synthesized from α,α-diphenyl-γ-butyrolactone and 4-(4-chlorophenyl)-4- hydroxypiperidine in five and four steps with 8% and 16% overall yield, respectively. The amide precursor was synthesized from 4-bromo-2,2- diphenylbutyronitrile and 4-(4-chlorophenyl)-4-hydroxypiperidine in 2 steps with 21-57% overall yield. [11C]N-Desmethyl-loperamide and [ 11C]loperamide were prepared from their corresponding amide precursor and N-desmethyl-loperamide with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 20-30% and 10-15% radiochemical yields, respectively, based on [11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.

A facile synthesis for novel loperamide analogs as potential μ opioid receptor agonists

A facile synthesis for novel loperamide analogs as potential μ opioid receptors is described. The synthetic procedure for compound 5, which contains two 4-phenyl piperidine scaffolds, was optimized, and this compound was synthesized in excellent yield. We