95558-32-0

Basic information

• Product Name: 1-benzyl-4-tosylpiperazine
• Synonyms: 1-benzyl-4-tosylpiperazine
• CAS NO: 95558-32-0
• Molecular Formula: C₁₈H₂₂N₂O₂S
• Molecular Weight: 330.44448
• Mol File: 95558-32-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-benzyl-4-tosylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-tosylpiperazine(95558-32-0)
• EPA Substance Registry System: 1-benzyl-4-tosylpiperazine(95558-32-0)

Safety Data

• Hazardous Substances Data: 95558-32-0(Hazardous Substances Data)

Upstream product

• 42137-88-2 N,N-bis(2-chloroethyl)-p-toluenesulfonamide 
• 100-46-9 benzylamine 
• 2759-28-6 1-phenylmethylpiperazine 
• 98-59-9 p-toluenesulfonyl chloride 
• 16695-22-0 N,N-bis(tosyloxyethyl)-p-toluenesulfonamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 212609-18-2 N-isopropyloxycarbonyl-N'-tozylpiperazine 
• 212609-19-3 N-cyclopentyloxycarbonyl-N'-tozylpiperazine 
• 2759-28-6 1-phenylmethylpiperazine 

Relevant articles and documents

Impact of N-substituents on crystal packing of N-alkyl-N′-tosylpiperazines and development of new polymorph of tosylbis(2-(tosyloxy)ethyl)amine: Synthesis, DFT, photophysical, cytotoxic property

Diethanol amine (DEA) was selected as a lead compound to prepare N-tosyldiethanol amine 1, N-tosylbis(2-(tosyloxy)ethyl)amine 2 and disubstituted piperazines ca N-alkyl-N′-tosylpiperazines 3–5 in high yield. The new compounds were characterized by using relevant techniques viz. MS, IR, 1H, 13C, DEPT 135 NMR, UV–vis. absorption and fluorescence spectral studies. Single crystal X-ray diffraction technique was used to detect a new polymorphic form of 2 and to measure the influence of various N-substituents on the association of molecules of 3–5 in the solid state. Evidently, the introduction of N-cyclohexyl substituent in 3 successfully switches off all the synthons ca CH…O and CH…N seen in compound 4 and 5. Compounds 4 and 5 holding N-furfuryl and N-benzyl substituents, respectively, adopt other packing strategies based on CH…O, CH…N (4) and CH…O (5) interactions. The antitumor activity of 1–5 was evaluated in vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Remarkably, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Density functional theory and molecular docking studies have been performed to rationalize the experimental results.

One-step cyclization: Synthesis of N -heteroalkyl-N′-tosylpiperazines

Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (SN) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.

Base-free monosulfonylation of amines using tosyl or mesyl chloride in water

A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.