1-(2-Methoxyphenyl)piperazine

Base Information

• Chemical Name: 1-(2-Methoxyphenyl)piperazine
• CAS No.: 35386-24-4
• Molecular Formula: C11H16N2O
• Molecular Weight: 192.261
• Hs Code.: 29349990
• European Community (EC) Number: 252-537-7
• UNII: 81NJO1330A
• DSSTox Substance ID: DTXSID40188871
• Nikkaji Number: J149.916E
• Wikidata: Q27072540
• Pharos Ligand ID: WDF54VDHX2LB
• ChEMBL ID: CHEMBL9666
• Mol file: 35386-24-4.mol

Synonyms:1-(2-methoxyphenyl)piperazine;1-(2-methoxyphenyl)piperazine dihydrochloride;1-(2-methoxyphenyl)piperazine hydrochloride;1-(ortho-methoxyphenyl)piperazine;o-methoxyphenylpiperazine

Chemical Property of 1-(2-Methoxyphenyl)piperazine

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid after melting
• Vapor Pressure: 5.68E-06mmHg at 25°C
• Melting Point: 35-40 °C(lit.)
• Refractive Index: n20/D 1.575(lit.)
• Boiling Point: 379.9 °C at 760 mmHg
• PKA: 8.98±0.10(Predicted)
• Flash Point: 154 °C
• PSA: 24.50000
• Density: 1.057 g/cm³
• LogP: 1.49860
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in chloroform, ethyl acetate, and methanol. Insoluble in water
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 192.126263138
• Heavy Atom Count: 14
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

1-(2-Methoxyphenyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-28A-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC=C1N2CCNCC2
• Recent ClinicalTrials: Evaluation of a Multi-phosphopeptide Vaccine Plus PolyICLC in Participants With High Risk and Advanced Malignancies
• Uses: A piperazine derivative and a selective antagonist at D3 receptors that influences the expression of cocaine-induced conditioned place preference (CPP). It is used as pharmaceutical intermediate. N-alkylated 1-(2-methyoxyphenyl)piperazines markedly improved affinity and selectivity of the dopamine D3 receptor which is recognized as a potential therapeutic target for the treatment of various neurological and psychiatric disorders. 1-(2-Methoxyphenyl)piperazine can be used:To functionalize pyrazolylvinyl ketones via Aza-Michael addition reaction.To prepare cyclic amine substituted Tr?ger′s base derivatives.To prepare functionalized bis(mercaptoimidazolyl)borates by reacting with the activated ester, [(1-methyl-2-mercaptoimidazol-5-yl)carbonyl]succinimide.

Technology Process of 1-(2-Methoxyphenyl)piperazine

There total 25 articles about 1-(2-Methoxyphenyl)piperazine 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: 100.0%

benzyl 4-(2-methoxyphenyl)piperazine-1-carboxylate → 1-(2-Methoxyphenyl)piperazine (35386-24-4)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 8h; chemoselective reaction;

DOI:10.1002/adsc.201700156

Reference yield: 94.0%

tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate (95520-98-2) → 1-(2-Methoxyphenyl)piperazine (35386-24-4)

Guidance literature:

tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate; With hydrogenchloride; In methanol; for 2h;

With sodium hydrogencarbonate; In water; Product distribution / selectivity;

Reference yield: 91.0%

piperazine (110-85-0) + 2-Chloroanisole (766-51-8) → 1-(2-Methoxyphenyl)piperazine (35386-24-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 0.166667h; Temperature;

DOI:10.1021/acs.orglett.6b02591

upstream raw materials:

bis(2-bromoethyl)amine hydrobromide

2-methoxy-phenylamine

piperazine

1,2-dimethoxybenzene

Downstream raw materials:

11-[4-(2-methoxy-phenyl)-piperazin-1-yl]-2-nitro-dibenzo[b,f][1,4]oxazepine

1-(6-chloro-2-methyl-1,1-dioxo-7-sulfamoyl-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-3-carbonyl)-4-(2-methoxy-phenyl)-piperazine

1-Chroman-3-yl-4-(2-methoxy-phenyl)-piperazine

Refernces

• 1、 Boursier, Michelle E.,Hall, Mary P.,Hurst, Robin,Killoran, Michael P.,Kirkland, Thomas A.,Levin, Sergiy,Machleidt, Thomas,Ohana, Rachel Friedman,Zimmerman, Kristopher. "An integrated approach toward nanobret tracers for analysis of gpcr ligand engagement". supporting information. . Retrieved 2021/05/31.
• 2、 Reilly, Sean W.,Riad, Aladdin A.,Hsieh, Chia-Ju,Sahlholm, Kristoffer,Jacome, Daniel A.,Griffin, Suzy,Taylor, Michelle,Weng, Chi-Chang,Xu, Kuiying,Kirschner, Nathan,Luedtke, Robert R.,Parry, Christopher,Malhotra, Shipra,Karanicolas, John,Mach, Robert H.. "Leveraging a Low-Affinity Diazaspiro Orthosteric Fragment to Reduce Dopamine D3 Receptor (D3R) Ligand Promiscuity across Highly Conserved Aminergic G-Protein-Coupled Receptors (GPCRs)". . p. 5132 - 5147. Retrieved 2019/05/28.