5368-33-2

Usage

Uses

Used in Pharmaceutical Research:
1-N-Benzyl-2-phenylpiperazine is used as a research compound for studying the effects of dopamine receptor agonism and its influence on other neurotransmitter systems in the brain. It aids in understanding the mechanisms of action and potential therapeutic applications in the treatment of psychiatric and neurological disorders.
Used in Neurotransmitter Receptor and Signaling Pathway Studies:
1-N-Benzyl-2-phenylpiperazine is utilized as a research tool to investigate neurotransmitter receptors and signaling pathways in the central nervous system. This helps in exploring the compound's potential role in modulating neurotransmission and its implications for the development of novel therapeutic agents.

InChI:InChI=1/C20H19N3O2S/c1-13-7-9-14(10-8-13)12-26-20-22-21-19(23(20)2)17-11-15-5-4-6-16(24-3)18(15)25-17/h4-11H,12H2,1-3H3

Synthetic route

1-benzyl-6-phenyl-piperazine-2,5-dione (1279816-48-6) → 1-benzyl-2-phenyl-piperazine (5368-33-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h;	90%

([benzyl-(tert-butylcarbamoyl-phenyl-methyl)-carbamoyl]-methyl)-carbamic acid tert-butyl ester (1296672-34-8) → 1-benzyl-2-phenyl-piperazine (5368-33-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 0.17 h / 180 °C / Microwave irradiation 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

benzaldehyde (100-52-7) → 1-benzyl-2-phenyl-piperazine (5368-33-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanol / 0.5 h / 20 °C 1.2: 20 °C 2.1: acetic acid / 0.17 h / 180 °C / Microwave irradiation 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

benzylamine (100-46-9) → 1-benzyl-2-phenyl-piperazine (5368-33-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanol / 0.5 h / 20 °C 1.2: 20 °C 2.1: acetic acid / 0.17 h / 180 °C / Microwave irradiation 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

Upstream product

• 1203590-31-1 4-benzyl-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester 
• 5271-26-1 m-phenylpiperazine 
• 502649-25-4 tert-butyl 4-(3-methoxy-4-(1H-pyrazol-4-yl)benzoyl)-3-phenylpiperazine-1-carboxylate 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 1279816-48-6 1-benzyl-6-phenyl-piperazine-2,5-dione 
• 1296672-34-8 ([benzyl-(tert-butylcarbamoyl-phenyl-methyl)-carbamoyl]-methyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Piperazine squaric acid diamides, a novel class of allosteric P2X7 receptor antagonists

The P2X7 receptor (P2X7R) stands out among the purinergic receptors due to its strong involvement in the regulation of tumor growth and metastasis formation as well as in innate immune responses and afferent signal transmission. Numerous studies have pointed out the beneficial effects of P2X7R antagonism for the treatment of a variety of cancer types, inflammatory diseases, and chronic pain. Herein we describe the development of novel P2X7R antagonists, incorporating piperazine squaric diamides as a central element. Besides improving the antagonists’ potency from pIC50 values of 5.7–7.6, ADME properties (logD7.4 value, plasma protein binding, in vitro metabolic stability) of the generated compounds were investigated and optimized to provide novel P2X7R antagonists with drug-like properties. Furthermore, docking studies revealed the antagonists binding to the allosteric binding pocket in two distinct binding poses, depending on the substitution of the central piperazine moiety.

A facile and rapid synthesis of N-benzyl-2-substituted piperazines

A facile and rapid synthetic approach of N-benzyl-2-substituted piperazine building-blocks via an Ugi strategy is described. This strategy is high yielding (80-92% overall yield), step-efficient and fast using microwave heating and tert-butylisocyanide as a convertible isocyanide. This method is useful for the obtention of key intermediates in medicinal chemistry.