56660-99-2

Basic information

• Product Name: 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol
• Synonyms: 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol;4-(p-Chlorophenyl)-1-[4,4-(ethylenebisoxy)-4-(p-fluorophenyl)butyl]-4-piperidinol
• CAS NO: 56660-99-2
• Molecular Formula: C₂₃H₂₇ClFNO₃
• Molecular Weight: 419.9168
• Mol File: 56660-99-2.mol

Chemical Properties

• Boiling Point: 549.1°Cat760mmHg
• Flash Point: 285.9°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 6.83E-13mmHg at 25°C
• Refractive Index: 1.572
• PKA: 13.87±0.20(Predicted)
• CAS DataBase Reference: 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol(56660-99-2)
• EPA Substance Registry System: 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol(56660-99-2)

Safety Data

• Hazardous Substances Data: 56660-99-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol is used as an intermediate in the synthesis of O-(1-(4-Fluorophenyl)butan-1-one) Haloperidol (F596225), which is an impurity of Haloperidol (H103700). Haloperidol is a medication with antidyskinetic and antipsychotic properties, utilized for the treatment of various conditions such as schizophrenia, bipolar disorder, and motor tics.
In the context of pharmaceutical chemistry, 4-(p-Chlorophenyl)-1-[3-[2-(p-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol serves as a crucial building block for the development of drugs with potential therapeutic benefits. Its synthesis and subsequent use in the production of Haloperidol highlight its importance in the medicinal chemistry field, where it contributes to the creation of medications that can help manage and alleviate the symptoms of various psychiatric disorders.

InChI:InChI=1/C23H27ClFNO3/c24-20-6-2-18(3-7-20)22(27)11-14-26(15-12-22)13-1-10-23(28-16-17-29-23)19-4-8-21(25)9-5-19/h2-9,27H,1,10-17H2

Upstream product

• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 3308-94-9 4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 847025-05-2 3-[2-(4-fluorophenyl)-[1,3]dioxolan-2-yl]propionic acid methyl ester 
• 847025-06-3 3-[2-(4-fluorophenyl)-[1,3]dioxolan-2-yl]propionaldehyde 

Downstream Products

• 52-86-8 haloperidol 

Relevant articles and documents

Stetter reaction in room temperature ionic liquids and application to the synthesis of haloperidol

Imidazolium-type room temperature ionic liquids (RTILs) have been used for the Stetter reaction, affording the desired 1,4-dicarbonyl compounds in good yields. Thiazolium salts and Et3N are efficient catalysts for this reaction performed in ionic liquid. The possibility to recycle and reuse the solvent has been demonstrated, although it was not possible to recycle the thiazolium catalyst. This method was used in the total synthesis of haloperidol.

Synthesis of High Specific Activity - and Bromperidol and Tissue Distribution Studies in the Rat

A rapid synthesis of - and bromperidol with specific activity exceeding 10 000 Ci/mmol is described in which a trimethylstannylated analogue of bromperidol is used as a substrate for regiospecific no-carrier-added radiobromination. 4--4-hydroxypiperidino>-4'-fluorobutyrophenone was synthesized by the reaction of (trimethylstannyl)sodium with haloperidol and purified by preparative HPLC.Subsequent radiobromination with no-carrier-added 75Br- or 77Br- and in situ oxidation using H2O2/CH3COOH gave a corrected radiochemical yield of 35percent with a 30-min preparation time.Tissue distribution studies in the rat show a rapid and prolonged uptake into the brain, liver, and kidneys and consistently low blood concentrations that differ quantitatively from previous studies using relatively low specific activity bromperidol.Potential clinical applications for this high specific activity radiobrominated neuroleptic are discussed.

The synthesis of [14C]-labelled haloperidol and [d4]- and [d8] haloperidol

The synthesis of [14C] haloperidol for use in metabolism studies, and the synthesis of [d4]- and [d8] haloperidol for use in bioavailability studies, is described.