63763-66-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyl-piperazine-1-carbonylchloride is used as a building block for the production of various drugs and agrochemicals. It is an important intermediate for the production of antipsychotic and antidepressant drugs due to its versatile reactivity and the presence of a carbonylchloride group in the molecule.
Used in Organic Chemistry Research:
4-Benzyl-piperazine-1-carbonylchloride is used as a research chemical in organic chemistry laboratories for the development of new chemical reactions and synthetic pathways, contributing to the advancement of organic chemistry and the discovery of novel compounds.

InChI:InChI=1/C12H15ClN2O/c13-12(16)15-8-6-14(7-9-15)10-11-4-2-1-3-5-11/h1-5H,6-10H2

Upstream product

• 2759-28-6 1-phenylmethylpiperazine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 148120-38-1 1-(phenylmethyl)-4-[(4'-methoxyphenyl)methyl]piperazine 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1416356-21-2 (E)-3,5,4'-tri[(N-benzylpiperazine-N'-carbonyl)oxy]stilbene 
• 1416355-88-8 (E)-(4-(3,5-dimethoxystyryl)phenyl) N-benzylpiperazine-N'-carboxylate 
• 75529-71-4 N,N-diethyl-N'-(4-(phenylmethyl)piperazinyl)urea 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 4'-aminochalcone-rivastigmine hybrids as multifunctional agents for the treatment of Alzheimer's disease

A series of 4'-aminochalcone-revastigmine hybrids were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease. The results showed that most of these compounds exhibited good multifunctional activities. In particular, compound 6c displayed the best inhibitory potency on acetylcholinesterase (IC50= 4.91 μM), and significant antioxidative activity with a value 2.83-fold of Trolox. The kinetic analysis of AChE inhibition revealed that 6c showed mixed-type inhibition, binding simultaneously to the catalytic active site and peripheral anionic site of AChE. In addition, 6c inhibited self-induced Aβ1-42aggregation and Cu2+-induced Aβ1-42aggregation by 89.5% and 79.7% at 25 μM respectively, as well as acted as a selective monoamine oxidase B inhibitor (IC50= 0.29 μM) and a selective biometal chelator. Furthermore, 6c could cross the blood-brain barrier in vitro. Based on these results, Compound 6c could be considered as a very promising lead compound for Alzheimer's disease.

Synthesis of 3- and 29-substituted celastrol derivatives and structure-activity relationship studies of their cytotoxic activities

A series of 3-carbamate and 29-ester celastrol derivatives (compounds 1–26) were designed and synthesized. These analogues were evaluated for their cytotoxic activities against several cancer cell lines. Cytotoxicity data revealed that the properties of substituents and substitution position had important influence on cytotoxic activity. Modification of C-3 hydroxyl with size-limited groups did not reduce the activity obviously. The introduction of polarity group like piperazine could improve the solubility. Compound 23 was chosen to further evaluate anti-tumor efficacy in vivo. It showed higher inhibition rate and better safety than celastrol during in vivo experiment by intragastric administration. The preliminary antitumor studies of compound 23 in vivo showed that it might be promising for the development of new antitumor agents.

Synthesis of pterostilbene and resveratrol carbamate derivatives as potential dual cholinesterase inhibitors and neuroprotective agents

Pterostilbene and resveratrol carbamate derivatives were designed and synthesized by use of a multi-target directed drug-design strategy. Their acetylcholinesterase and butylcholinesterase inhibitory activity and neuroprotective effects against hydrogen peroxide-induced PC12 cell injury were evaluated in vitro. The results indicated that some of the compounds had dual inhibitory potency against acetylcholinesterase and butylcholinesterase, and potential neuroprotective effects, and could be considered as potential multi-target-directed agents.

Debenzylation of tertiary amines using phosgene or triphosgene: An efficient and rapid procedure for the preparation of carbamoyl chlorides and unsymmetrical ureas. Application in carbon-11 chemistry

Efficient and rapid preparations of carbamoyl chlorides and unsymmetrical ureas from tertiary amines and phosgene or its safe equivalent triphosgene [bis(trichloromethyl)carbonate, BTC] are described. First, the reaction of stoichiometric amounts of phosgene with secondary amines was revisited, and it was shown that the formation of carbamoyl chlorides in high yields required careful adjustments of experimental conditions and the use of pyridine as an HCl scavenger. A phosgene-mediated dealkylation of triethylamine was observed when this base was used instead of pyridine. Taking advantage of this observation, a strategy of synthesis of carbamoyl chlorides from tertiary amines and phosgene has been developed. N-Alkyl-N-benzyl(substituted)tetrahydroisoquinolines, -piperazines, -piperidines, or -anilines were treated with stoichiometric amounts of phosgene (or BTC) in CH2Cl2. Tertiary amines bearing electron-enriched benzyl group(s) afforded carbamoyl chlorides in excellent yields and without any contamination by symmetrical ureas. Subsequent additions of primary or secondary amines to these carbamoyl chlorides produced unsymmetrical ureas in single-pot and high-yielding operations. This methodology was applied in 11C-chemistry. From [ 11C]phosgene, a common precursor used in the preparation of radiotracers for positron emission tomography, a rapid and efficient synthesis of 11C-carbamoyl chlorides and 11C-unsymmetrical ureas derived from tetrahydroisoquinoline and piperazine is described. The first example of 11C-amide formation from the reaction of a 11C-carbamoyl chloride and an organometallic (cyanocuprate or a Grignard reagent in the presence of a nickel catalyst) is also presented.