3074-46-2

Basic information

• Product Name: 1-BENZYL-4-PHENYLPIPERAZINE
• Synonyms: 1-BENZYL-4-PHENYLPIPERAZINE
• CAS NO: 3074-46-2
• Molecular Formula: C₁₇H₂₀N₂
• Molecular Weight: 252.35
• Product Categories: Piperaizine;Piperazines
• Mol File: 3074-46-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 376.1 °C at 760 mmHg
• Flash Point: 167.1 °C
• Appearance: /
• Density: 1.092 g/cm³
• Vapor Pressure: 7.4E-06mmHg at 25°C
• Refractive Index: 1.601
• PKA: 7.59±0.10(Predicted)
• CAS DataBase Reference: 1-BENZYL-4-PHENYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-4-PHENYLPIPERAZINE(3074-46-2)
• EPA Substance Registry System: 1-BENZYL-4-PHENYLPIPERAZINE(3074-46-2)

Safety Data

• Hazardous Substances Data: 3074-46-2(Hazardous Substances Data)

Usage

General Description

1-BENZYL-4-PHENYLPIPERAZINE is a chemical compound with the formula C20H24N2. It is a piperazine derivative, specifically a benzyl-substituted analog of the compound 1-phenylpiperazine. 1-BENZYL-4-PHENYLPIPERAZINE has been studied for its potential pharmacological activity, including as a potential antipsychotic and antidepressant. Its structure suggests that it may interact with serotonin and dopamine receptors in the central nervous system, which are known to be involved in mood regulation and psychiatric disorders. Further research is needed to fully understand the potential therapeutic applications of 1-BENZYL-4-PHENYLPIPERAZINE and its mechanism of action.

InChI:InChI=1/C17H20N2/c1-3-7-16(8-4-1)15-18-11-13-19(14-12-18)17-9-5-2-6-10-17/h1-10H,11-15H2

Synthetic route

polymer, polymerization degree = 50; monomer(s): (1S,2R,6S,7R)-4-benzyl-4-thionia-tricyclo[5.2.1.02,6]dec-8-ene perchlorate + 4-phenyl-1-piperazine (92-54-6) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With caesium carbonate; sodium iodide In dichloromethane at 80℃; for 1h;	98%

4-phenyl-1-piperazine (92-54-6) + benzaldehyde (100-52-7) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
Stage #1: 4-phenyl-1-piperazine; benzaldehyde for 0.0666667h; Microwave irradiation; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.5h;	98%
With sodium cyanoborohydride; acetic acid In methanol; 1,2-dichloro-ethane at 65℃; for 0.166667h; Flow reactor;

4-phenyl-1-piperazine (92-54-6) + silica-supported oligomeric benzyl phosphate → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With caesium carbonate; sodium iodide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Sealed tube;	95%

4-phenyl-1-piperazine (92-54-6) + polymer, degree of polymerization 60; monomer(s): 2-chlorosulfonyl-5-norbornene; ethyl vinyl ether; benzyl alcohol → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With triethylamine In dichloromethane at 40℃;	94%

4-phenyl-1-piperazine (92-54-6) + benzyl bromide (100-39-0) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
In dimethyl sulfoxide	89%
With sodium carbonate In acetonitrile at 20℃;	84%
With aluminum oxide; potassium carbonate for 0.0833333h; Solid phase reaction; alkylation; microwave irradiation;	74%

formaldehyd (50-00-0) + bromobenzene (108-86-1) + 4-phenyl-1-piperazine (92-54-6) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With cobalt(II) bromide; zinc In acetonitrile at 60℃; for 1.5h; Mannich type reaction; Inert atmosphere;	89%

4-phenyl-1-piperazine (92-54-6) + benzyl chloride (100-44-7) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With potassium carbonate In butanone at 80℃; for 24h;	82%
With toluene

4-phenyl-1-piperazine (92-54-6) + benzyl alcohol (100-51-6) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With iron(III)phthalocyanine chloride; potassium tert-butylate In neat (no solvent) at 170℃; for 24h; Inert atmosphere; Microwave irradiation;	82%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + iodobenzene (591-50-4) + benzyl bromide (100-39-0) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 65℃; for 4h; Solvent; Temperature; Inert atmosphere;	79%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + iodobenzene (591-50-4) + benzyl chloride (100-44-7) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 65℃; for 4h; Inert atmosphere;	78%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + bromobenzene (108-86-1) + benzyl bromide (100-39-0) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 65℃; for 4h; Inert atmosphere;	75%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + bromobenzene (108-86-1) + benzyl chloride (100-44-7) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 65℃; for 4h; Inert atmosphere;	74%

2-(4-benzyl-piperazin-1-yl)-benzaldehyde (112253-26-6) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; (1S)-10-camphorsulfonic acid In toluene at 140℃; under 760.051 Torr; for 18h; Sealed tube; Molecular sieve;	11%

bromobenzene (108-86-1) + 1-phenylmethylpiperazine (2759-28-6) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With palladium diacetate; sodium t-butanolate; DavePhos In toluene at 110℃; for 20h;	96 % Chromat.

4-phenyl-1-piperazine (92-54-6) + C16H19O4P (1233656-18-2) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
Stage #1: C16H19O4P With Grubbs catalyst first generation In dichloromethane at 50℃; Inert atmosphere; Stage #2: 4-phenyl-1-piperazine With tetra-(n-butyl)ammonium iodide; potassium carbonate In chloroform at 80℃; Inert atmosphere;

benzyl chloride (100-44-7) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: neat (no solvent) / 0.25 h 2: lithium tert-butoxide; copper(l) chloride / 1-methyl-pyrrolidin-2-one / 14 h / 70 °C View Scheme

Phenyl triflate (17763-67-6) + 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride (42790-42-1) → N-benzyl,N'-phenylpiperazine (3074-46-2)

Conditions	Yield
With copper(l) chloride; lithium tert-butoxide In 1-methyl-pyrrolidin-2-one at 70℃; for 14h;

N-benzyl,N'-phenylpiperazine (3074-46-2) → 4-benzyl-1-phenylpiperazine-2,3-dione (206753-52-8)

Conditions	Yield
Stage #1: N-benzyl,N'-phenylpiperazine With sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 0℃; for 0.0833333h; Stage #2: With sodium hypochlorite; sodium chlorite In water; acetonitrile	75%

N-benzyl,N'-phenylpiperazine (3074-46-2) + 2-(4-methoxyphenyl)-1-tosylaziridine (155721-36-1) → C33H37N3O3S + C33H37N3O3S

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In toluene at 23℃; for 36h; Inert atmosphere; Overall yield = 88 %; Overall yield = 48.8 mg;	A n/a B n/a

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 108-86-1 bromobenzene 
• 2759-28-6 1-phenylmethylpiperazine 
• 50-00-0 formaldehyd 
• 1233656-18-2 C₁₆H₁₉O₄P 
• 100-52-7 benzaldehyde 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 591-50-4 iodobenzene 
• 17763-67-6 Phenyl triflate 
• 42790-42-1 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride 
• 112253-26-6 2-(4-benzyl-piperazin-1-yl)-benzaldehyde 
• 100-51-6 benzyl alcohol 

Downstream Products

• 206753-52-8 4-benzyl-1-phenylpiperazine-2,3-dione 

Relevant articles and documents

A short and efficient synthesis of N-aryl- and N-heteroaryl-N′- (arylalkyl)piperazines

A new synthesis of N-aryl- and N-heteroaryl-N′-(arylalkyl) piperazines using palladium-catalyzed amination of aryl bromides and heteroaryl chlorides with mono N-benzyl- or N-(arylethyl)piperazines is reported. Most coupling processes proceed in high yield and good selectivity using either diadamantyl-n-butylphosphine (1), 2-(dicyclohexylphosphino)-2′-(N,N- dimethylamino)biphenyl (2), or 2-(di-tert-butylphosphino)biphenyl (3) as ligand. Applying an automated parallel synthesizer the preparation of a small library of potentially bioactive compounds is easily achieved.

Synthesis of N-alkyl-N′-aryl or Alkenylpiperazines: A Copper-Catalyzed C–N Cross-Coupling in the Presence of Aryl and Alkenyl Triflates and DABCO

Unsymmetrical piperazines are key constituents of many pharmaceuticals. Given that the selective introduction of an aryl and alkyl motif onto the piperazine is not always straightforward, direct arylation and alkenylation of 1,4-diaza-bicyclo[2.2.2]octane would obviate the inefficiencies associated with the preparation of these target molecules. We have utilized alkyl halides, aryl or alkenyl triflates, and 1,4-diaza-bicyclo[2.2.2]octane for the synthesis of N-alkyl-N′-aryl or alkenylpiperazines. The optimum conditions are developed using CuCl, t-BuOLi in NMP. Alkenyl triflates requires N,N′-dimethylethylenediamine and higher temperature to afford the desired cross-coupled product. Substrates bearing electron-deficient and electron-rich groups were successfully coupled under the optimum reaction conditions.

A segmented flow platform for on-demand medicinal chemistry and compound synthesis in oscillating droplets

We report an automated flow chemistry platform that can efficiently perform a wide range of chemistries, including single/multi-phase and single/multi-step, with a reaction volume of just 14 μL. The breadth of compatible chemistries is successfully demonstrated and the desired products are characterized, isolated, and collected online by preparative HPLC/MS/ELSD.