148245-18-5

Basic information

• Product Name: 1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE
• Synonyms: TIMTEC-BB SBB011449;1-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)PIPERAZINE;1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE;1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE DIHYDROCHLORIDE;AKOS BB-5568;BUTTPARK 121\50-51;OTAVA-BB 1047751;1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)piperazine
• CAS NO: 148245-18-5
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• Mol File: 148245-18-5.mol

Chemical Properties

• Boiling Point: 402.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.180±0.06 g/cm3(Predicted)
• PKA: 8.91±0.10(Predicted)
• CAS DataBase Reference: 1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE(148245-18-5)
• EPA Substance Registry System: 1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-PIPERAZINE(148245-18-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 148245-18-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazin is used as a potential therapeutic agent for the treatment of various psychiatric and neurological disorders due to its ability to interact with neurotransmitter receptors in the brain and its potential to modulate dopamine and serotonin levels.
Used in Research and Development:
In the field of medicinal chemistry, 1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazin serves as a subject of ongoing research to understand its pharmacological properties, which may lead to the development of new drugs for the treatment of mental health conditions.

Upstream product

• 493-09-4 benzo-1,4-dioxane 
• 140681-55-6 Selectfluor 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 22013-33-8 6-amino-3,4-benzodioxane 
• 52287-51-1 6-bromo-1,4-benzodioxane 
• 750573-08-1 tert-butyl 4-(2H,3H-benzo[e]-1,4-dioxin-6-yl)piperazinecaboxylate 

Downstream Products

• 1328317-21-0 (4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)piperazine-1-yl)(4-fluorophenyl)methanone 
• 1535195-96-0 (4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)piperazine-1-yl)(4-nitrophenyl)methanone 
• 1350900-68-3 5-((4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)piperazin-1-yl)-methyl)-2-fluorophenol 
• 1535195-92-6 1-(3-(benzyloxy)-4-fluorobenzyl)-4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)piperazine 
• 1350900-66-1 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-(4-fluoro-3-methoxybenzyl)piperazine 
• 1350900-75-2 6-(4-[4-[¹⁸F]fluorobenzyl]piperazine-1-yl)benzodioxin 
• 1610471-65-2 C₁₉H₁₉⁽¹⁸⁾FN₂O₃ 
• 1350900-76-3 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-(4-[¹⁸F]fluoro-3-methoxybenzyl)piperazine 
• 1350900-77-4 6-(4-[4-[¹⁸F]fluoro-3-hydroxybenzyl]piperazine-1-yl)benzodioxin 
• 1535195-99-3 C₂₆H₂₇⁽¹⁸⁾FN₂O₃ 
• 253689-49-5 1-(1,4-benzodioxan-6-yl)-4-(4-fluorobenzyl)piperazine oxalate 

Relevant articles and documents

Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine

Reaction of a series of bicyclic bromoarenes with N-tert- butoxycarbonylpiperazine (N-Boc-piperazine) under palladium-catalysed coupling conditions followed by routine removal of the Boc group with trifluoroacetic acid in dichloromethane gave the corresponding arylpiperazines in moderate to good yield.

Arene Amination Instead of Fluorination: Substitution Pattern Governs the Reactivity of Dialkoxybenzenes with Selectfluor

Arene substitution patterns are well-known to affect the regioselectivity of a given transformation but not necessarily the type of reactivity. Herein, we report that the substitution pattern of alkoxyarenes dictates whether a putative one-electron or two

Labeling of benzodioxin piperazines with fluorine-18 as prospective radioligands for selective imaging of dopamine D4 receptors

The D4 receptor is of high interest for research and clinical application but puts high demands on appropriate radioligands to be useful tools for investigation. Search for adequate radioligands suitable for in vivo imaging is therefore still in progress. The potential neuroleptic drug 6-(4-[4-fluorobenzyl]piperazin-1-yl)benzodioxin shows high affinity and selectivity to the D4 receptor. Derivatization of this lead structure by adding hydrophilic moieties was carried out in order to lower its lipophilicity what led to three new putative dopamine receptor D4 ligands. A comprehensive description of the syntheses of standard compounds and corresponding labeling precursors is given which were obtained in satisfactory yields. Furthermore, the radiosyntheses by direct 18F-labeling and build-up synthesis were compared. All derivatives of 6-(4-[4-fluorobenzyl]- piperazin-1-yl)benzodioxin were successfully synthesized in 18F- labeled form with radiochemical yields of 9-35% and molar activities of 30-60 GBq/μmol using one-pot procedures. 2013 John Wiley & Sons, Ltd. Derivatives of the lead structure 6-(4-[4-fluorobenzyl]-piperazine-1-yl) benzodioxin were successfully synthesized, labeled via direct 18F-substitution or build-up synthesis leading to new putative radioligands for imaging of the dopamine D4 receptor. Reductive amination proved as the method of choice for preparation of substituted benzyl-derivatives of piperazine as precursors and standards, and also superior for build-up radiofluorination (RCY = 9 - 35;%) in comparison to direct 18F- labeling (RCY = 1 - 5;%).

Discovery of small molecules that inhibit melanogenesis via regulation of tyrosinase expression

5,6,7,8-Tetrahydro-4H-cyclohepta[d]isoxazole derivatives were synthesized and evaluated as a novel class of inhibitors for α-melanocyte-stimulating hormone (α-MSH) induced melanogenesis in a mouse melanoma B16F10 cell line. Compound 8e (IC50 = 0.67 μM), 8h (IC50 = 1.01 μM) and 9b (IC50 = 0.99 μM) exhibited a potent inhibitory activity approximately 85- to 126-fold greater than kojic acid, a well-known potent inhibitor. A biochemical study indicates that the activity of this series should be displayed via down-regulation of the expression of tyrosinase.

6-(4-arylalkylpiperazin-1-yl) benzodioxane and 6-(4-arylalkylpiperazin-1-yl) chromane derivatives: dopamine receptor subtype specific ligands

Disclosed are compounds of the formula: or the pharmaceutically acceptable acid addition salts thereof wherein: R1, R2, R3, R4and R5are the same or different and represent hydrogen, halogen, C1/

6-(4-Benzylpiperazin-1-yl)benzodioxanes as selective ligands at cloned primate dopamine D4 receptors

A series of novel 6-(4-benzylpiperazin-1-yl)benzodioxanes were prepared and screened at selected dopamine receptor subtypes. 6-(4-[4-Chlorobenzyl]piperazin-1-yl)benzodioxane (2d) had high affinity and selectivity for the D4 dopamine receptor su