N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide

Base Information

• Chemical Name: N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide
• CAS No.: 190383-31-4
• Molecular Formula: C₂₀H₂₂N₄O
• Molecular Weight: 334.421
• UNII: 2A5XS99U8Q
• DSSTox Substance ID: DTXSID7044007
• Nikkaji Number: J847.821J
• Wikipedia: PD-168,077
• Wikidata: Q7118743
• Pharos Ligand ID: A1LK5YHLDNF4
• ChEMBL ID: CHEMBL45244
• Mol file: 190383-31-4.mol

Synonyms:N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide;N-(4-2-cyanophenylpiperazin-1-ylmethyl)-3-methylbenzamide maleate;PD 168,077;PD 168077;PD-168,077;PD-168077;PD168,077;PD168077

Chemical Property of N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide

Chemical Property:

• Vapor Pressure: 2.43E-12mmHg at 25°C
• Boiling Point: 554.6°C at 760 mmHg
• PKA: 14.89±0.46(Predicted)
• Flash Point: 289.2°C
• PSA: 133.97000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 2.48178
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.17936134
• Heavy Atom Count: 25
• Complexity: 491

Purity/Quality:

97% ^*data from raw suppliers

PD168077 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C(=O)NCN2CCN(CC2)C3=CC=CC=C3C#N
• Uses: The dopamine receptors play important role in cognition, memory, learning, and motor control (1). These receptors have been implicated as a therapeutic target for many psychiatric and neurological disorders. PD 168077 is a D4 dopamine receptor agonist and can be used to study ligand-receptor interactions of dopamine receptors (2).

Technology Process of N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide

There total 3 articles about N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

[(3-methylbenzoyl)amino]methyl acetate (630117-18-9) + 2-(piperazin-1-yl)benzonitrile (111373-03-6) → N-([4-(2-cyanophenyl)piperazin-1-yl]methyl)-3-methylbenzamide (190383-31-4)

Guidance literature:

[(3-methylbenzoyl)amino]methyl acetate; 2-(piperazin-1-yl)benzonitrile; With sodium hydride; In mineral oil;

With maleic acid; In isopropyl alcohol; mineral oil; Heating;

DOI:10.1007/s11172-011-0250-4

Reference yield:

N-(3-Methylbenzoyl)glycine (27115-49-7) → N-([4-(2-cyanophenyl)piperazin-1-yl]methyl)-3-methylbenzamide (190383-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Pb(OAc)4 / benzene / 4 h / Heating

2: Et₃N / acetonitrile / 4 h / 25 °C

With lead(IV) acetate; triethylamine; In acetonitrile; benzene;

DOI:10.1021/jm970021c

Reference yield:

3-Methylbenzoyl chloride (1711-06-4) → N-([4-(2-cyanophenyl)piperazin-1-yl]methyl)-3-methylbenzamide (190383-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2N aq. NaOH / CH₂Cl₂ / 4 h / 25 °C

2: Pb(OAc)4 / benzene / 4 h / Heating

3: Et₃N / acetonitrile / 4 h / 25 °C

With lead(IV) acetate; sodium hydroxide; triethylamine; In dichloromethane; acetonitrile; benzene;

DOI:10.1021/jm970021c

upstream raw materials:

[(3-methylbenzoyl)amino]methyl acetate

2-(piperazin-1-yl)benzonitrile

N-(3-Methylbenzoyl)glycine

3-Methylbenzoyl chloride