444582-90-5

Basic information

• Product Name: 1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE
• Synonyms: 4-(2-Carboxyphenyl)piperazine, N1-BOC protected, tert-Butyl 4-(2-carboxyphenyl)piperazine-1-carboxylate;1-(2-carboxyphenyl)-4-Boc piperazine;2-(4-(tert-Butoxycarbonyl);4-(2-Carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester;4-(2-CARBOXYPHENYL)PIPERAZINE, 1-BOC PROTECTED;2-[4-(TERT-BUTOXYCARBONYL)PIPERAZIN-1-YL]BENZOIC ACID;2-[4-(TERT-BUTOXYCARBONYL)PIPERAZINO]BENZOIC ACID;1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE
• CAS NO: 444582-90-5
• Molecular Formula: C₁₆H₂₂N₂O₄
• Molecular Weight: 306.36
• Mol File: 444582-90-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 165 °C
• Boiling Point: 458.9 °C at 760 mmHg
• Flash Point: 231.4 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 3.23E-09mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE(444582-90-5)
• EPA Substance Registry System: 1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE(444582-90-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 444582-90-5(Hazardous Substances Data)

Usage

General Description

1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE is a compound with the chemical formula C16H22N2O4. It is commonly used as a building block in organic synthesis, particularly in the pharmaceutical industry to create a variety of potential drug candidates. The compound contains a piperazine ring with a 2-carboxyphenyl group and a tert-butoxycarbonyl (BOC) protecting group. The BOC group is often used to protect amine groups during chemical reactions, and can be removed under mild conditions to expose a reactive amine functionality. 1-BOC-4-(2-CARBOXYPHENYL)PIPERAZINE is an important intermediate for the synthesis of various pharmaceuticals and biologically active compounds.

InChI:InChI=1/C16H22N2O4/c1-16(2,3)22-15(21)18-10-8-17(9-11-18)13-7-5-4-6-12(13)14(19)20/h4-7H,8-11H2,1-3H3,(H,19,20)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 446831-27-2 2-(piperazin-1-yl)benzoic acid 
• 111373-03-6 2-(piperazin-1-yl)benzonitrile 
• 174855-57-3 tert-butyl 4-(2-formylphenyl)piperazinecarboxylate 

Downstream Products

• 179250-28-3 4-(2-(hydroxymethyl)phenyl)piperazine-1-carboxylic acid tert-butyl ester 
• 209160-88-3 1-t-butoxycarbonyl-4-(2-(methanesulfonyloxymethyl)phenyl)-piperazine 
• 179250-29-4 1-tert-butoxycarbonyl-4-(2-(imidazol-1-ylmethyl)phenyl)piperazine 
• 444582-00-7 1-tert-butoxycarbonyl-4-[2-((2-methylimidazol-1-yl)methyl)phenyl]piperazine 
• 1253936-71-8 4-[2-(2-amino-4-trifluoromethyl-phenylcarbamoyl)phenyl]piperazine-1-carboxylic acid tert-butyl ester 
• 1253383-94-6 4-[2-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1253936-87-6 2-(3,5-dimethyl-pyrazol-1-yl)-1-{4-[2-(5-trifluoromethyl-1H-benzoimidazol-2-yl)phenyl]piperazin-1-yl}ethanone 
• 1253936-72-9 N-(2-amino-4-trifluoromethyl-phenyl)-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)acetyl]piperazin-1-yl}benzamide 

Relevant articles and documents

CXCR3 RECEPTOR ANTAGONISTS

The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1 to R6, A, B, X, Y and n are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

Synthesis and Structure-Activity Relationships of Novel Arylpiperazines as Potent and Selective Agonists of the Melanocortin Subtype-4 Receptor

The melanocortin receptors have been implicated as potential targets for a number of important therapeutic indications, including inflammation, sexual dysfunction, and obesity. We identified compound 1, an arylpiperazine attached to the dipeptide H-D-Tic-D-p-Cl-Phe-OH, as a novel melanocortin subtype-4 receptor (MC4R) agonist through iterative directed screening of nonpeptidyl G-protein-coupled receptor biased libraries. Structure-activity relationship (SAR) studies demonstrated that substitutions at the ortho position of the aryl ring improved binding and functional potency. For example, the o-isopropyl-substituted compound 29 (Ki = 720 nM) possessed 9-fold better binding affinity compared to the unsubstituted aryl ring (Ki = 6600 nM). Sulfonamide 39 (Ki = 220 nM) fills this space with a polar substituent, resulting in a further 2-fold improvement in binding affinity. The most potent compounds such as the diethylamine 44 (Ki = 60 nM) contain a basic group at this position. Basic heterocycles such as the imidazole 50 (Ki = 110 nM) were similarly effective. We also demonstrated good oral bioavailability for sulfonamide 39.