1-Acetyl-4-(4-hydroxyphenyl)piperazine

Base Information

• Chemical Name: 1-Acetyl-4-(4-hydroxyphenyl)piperazine
• CAS No.: 67914-60-7
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.271
• Hs Code.: 29214910
• European Community (EC) Number: 267-744-8
• UNII: YH9GD5K5NY
• DSSTox Substance ID: DTXSID3057804
• Nikkaji Number: J287.743K
• Wikidata: Q27455472
• ChEMBL ID: CHEMBL202608
• Mol file: 67914-60-7.mol

Synonyms:1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone

Chemical Property of 1-Acetyl-4-(4-hydroxyphenyl)piperazine

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 5.91E-09mmHg at 25°C
• Melting Point: 180-185 °C(lit.)
• Refractive Index: 1.584
• Boiling Point: 456.5 °C at 760 mmHg
• PKA: 12.18±0.30(Predicted)
• Flash Point: 229.9 °C
• PSA: 43.78000
• Density: 1.207 g/cm³
• LogP: 1.06360
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 4.3 g/L (20 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 220.121177757
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

1-Acetyl-4-(4-hydroxyphenyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)O
• Uses: 1-Acetyl-4-(4-hydroxyphenyl)piperazine may be used in the preparation of 1-acetyl-4-(4-octadecyloxyphenyl)piperazine. It may also be used in the multi-step synthesis of ketoconazole, its 1,2,4-triazole and thiazole analogs.

Technology Process of 1-Acetyl-4-(4-hydroxyphenyl)piperazine

There total 11 articles about 1-Acetyl-4-(4-hydroxyphenyl)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: 92.0%

1-(4-Acetoxyphenyl)-4-acetylpiperazine (133345-21-8) → N-acetyl-N'-(4-hydroxyphenyl)piperazine (67914-60-7,89929-31-7)

Guidance literature:

With water; potassium hydrogencarbonate; In methanol; Ambient temperature;

DOI:10.1002/ardp.19923251102

Reference yield: 54.0%

1-(4-hydroxyphenyl)piperazine (56621-48-8) + acetic anhydride (108-24-7) → N-acetyl-N'-(4-hydroxyphenyl)piperazine (67914-60-7,89929-31-7)

Guidance literature:

1-(4-hydroxyphenyl)piperazine; acetic anhydride; With pyridine; at 0 - 20 ℃; for 3.08333h;

With methanol; water; potassium carbonate; for 1.5h;

With hydrogenchloride; water; In dichloromethane; pH=3;

Reference yield:

ammonium hydroxide (1336-21-6) + diethylazodicarboxylate (1972-28-7,218603-74-8) → N-acetyl-N'-(4-hydroxyphenyl)piperazine (67914-60-7,89929-31-7)

Guidance literature:

With sodium hydroxide; oxalic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

upstream raw materials:

1-(4-Acetoxyphenyl)-4-acetylpiperazine

1-(4-hydroxyphenyl)piperazine

4-(4-methoxyphenyl)piperazine

1-(4-hydroxy-phenyl)-piperazine dihydrobromide

Downstream raw materials:

ketoconazole

(+/-)-1-acetyl-4-<4-(2,3-dihydroxypropoxy)phenyl>piperazine

4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine

cis-1-<4-<<2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>piperazine

Refernces

• 1、 Pagano, Mafalda,Castagnolo, Daniele,Bernardini, Martina,Fallacara, Anna Lucia,Laurenzana, Ilaria,Deodato, Davide,Kessler, Ulrich,Pilger, Beatrice,Stergiou, Lilli,Strunze, Stephan,Tintori, Cristina,Botta, Maurizio. "The fight against the influenza A virus H1N1: Synthesis, molecular modeling, and biological evaluation of benzofurazan derivatives as viral RNA polymerase inhibitors". . p. 129 - 150. Retrieved 2014/01/17.
• 2、 Power, Eoin C.,Ganellin, C. Robin,Benton, David C.H.. "Partial structures of ketoconazole as modulators of the large conductance calcium-activated potassium channel (BKCa)". . p. 887 - 890. Retrieved 2007/10/03.