117009-97-9

Basic information

• Product Name: BENZYL 1-HOMOPIPERAZINECARBOXYLATE
• Synonyms: Benzyl 1,4-diazepane-1-carboxylate;1,4-Diazepane, N1-CBZ protected;Homopiperazine, N1-CBZ protected, Benzyl 1,4-diazepane-1-carboxylate, Benzyl homopiperazine-1-carboxylate;1-(Benzyloxycarbonyl)hoMopiperazine, 96%;Benzyl 1-hoMopiperazinecarboxylate;Benzyl 1-homopiperazinecarboxylate 96%;2-benzyl-1,4-diazepane-1-carboxylate;1H-1,4-Diazepine-1-carboxylicacid, hexahydro-, phenylmethyl ester
• CAS NO: 117009-97-9
• Molecular Formula: C₁₃H₁₈N₂O₂
• Molecular Weight: 234.29422
• EINECS: 231-313-2
• Product Categories: API intermediates
• Mol File: 117009-97-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 130 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.42±0.20(Predicted)
• CAS DataBase Reference: BENZYL 1-HOMOPIPERAZINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 1-HOMOPIPERAZINECARBOXYLATE(117009-97-9)
• EPA Substance Registry System: BENZYL 1-HOMOPIPERAZINECARBOXYLATE(117009-97-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 117009-97-9(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

InChI:InChI=1/C13H18N2O2/c16-13(15-9-4-7-14-8-10-15)17-11-12-5-2-1-3-6-12/h1-3,5-6,14H,4,7-11H2

Upstream product

• 505-66-8 1,4-Diazacycloheptane 
• 501-53-1 benzyl chloroformate 
• 18158-16-2 benzyl 5-oxo-1,4-diazepane-1-carboxylate 
• 1208098-44-5 benzyl 4-(hydroxyimino)piperidine-1-carboxylate 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 41979-39-9 4-piperidone hydrochloride 
• 112275-50-0 tert-butyl 1,4-diazepine-1-carboxylate 

Downstream Products

• 336191-56-1 4-(2-ethoxycarbonyl-ethyl)-[1,4]diazepane-1-carboxylic acid benzyl ester 
• 336191-60-7 benzyl 4-(3-ethoxy-3-oxopropanoyl)-1,4-diazepane-1-carboxylate 
• 105628-07-7 fasudil hydrochloride 
• 186544-80-9 C₂₂H₂₃N₃O₄S 
• 868066-28-8 benzyl 4-[4-(2,2,2-trifluoroacetyl)phenyl]-1,4-diazepane-1-carboxylate 

Relevant articles and documents

Design and Scalable Synthesis of N-Alkylhydroxylamine Reagents for the Direct Iron-Catalyzed Installation of Medicinally Relevant Amines**

Secondary and tertiary alkylamines are privileged substance classes that are often found in pharmaceuticals and other biologically active small molecules. Herein, we report their direct synthesis from alkenes through an aminative difunctionalization reaction enabled by iron catalysis. A family of ten novel hydroxylamine-derived aminating reagents were designed for the installation of several medicinally relevant amine groups, such as methylamine, morpholine and piperazine, through the aminochlorination of alkenes. The method has excellent functional group tolerance and a broad scope of alkenes was converted to the corresponding products, including several drug-like molecules. Besides aminochlorination, the installation of other functionalities through aminoazidation, aminohydroxylation and even intramolecular carboamination reactions, was demonstrated, further highlighting the broad potential of these new reagents for the discovery of novel amination reactions.

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

Mono-acylation of piperazine and homopiperazine via ionic immobilization

A method for the selective mono-acylation of piperazine and homopiperazine has been developed. In a flow system, initially the diamine is ionically immobilized on a sulfonic acid funtionalized silica gel, acylated with an appropriate reagent and finally liberated with ammonic methanol. Examples with high yield and purity are presented.