Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate

Base Information

• Chemical Name: Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate
• CAS No.: 184177-81-9
• Molecular Formula: C23H23 N3 O3
• Molecular Weight: 389.454
• Hs Code.: 2933599090
• European Community (EC) Number: 606-021-7
• DSSTox Substance ID: DTXSID10361710
• Wikidata: Q27212868
• ChEMBL ID: CHEMBL1326856
• Mol file: 184177-81-9.mol

Synonyms:184177-81-9;Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate;phenyl N-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]carbamate;phenyl {4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}carbamate;SMR000073777;MLS000062853;phenyl {4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl}carbamate;N-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]carbamic acid phenyl ester;phenyl 4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenylcarbaMate;MLS002541909;SCHEMBL3898025;CHEMBL1326856;BDBM62766;cid_1317528;DTXSID10361710;CHEBI:123196;HMS2495J06;AMY14801;MFCD03784249;STK147738;[4-[4-(4-Hydroxyphenyl)-1-piperazinyl]phenyl]carbamic acid phenyl ester;AKOS000427516;AC-28752;DS-18226;CS-0010883;A880789;Q27212868;Phenyl(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate;N-[4-[4-(4-hydroxyphenyl)piperazino]phenyl]carbamic acid phenyl ester;CarbaMic acid, [4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-, phenyl ester (9CI);CarbaMic acid,[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-,phenyl ester (9CI)

Chemical Property of Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate

Chemical Property:

• Vapor Pressure: 3.52E-15mmHg at 25°C
• Refractive Index: 1.67
• Boiling Point: 603.9°C at 760 mmHg
• PKA: 12.18±0.30(Predicted)
• Flash Point: 319°C
• PSA: 65.04000
• Density: 1.296
• LogP: 4.53270
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 389.17394160
• Heavy Atom Count: 29
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

[4-[4-(4-Hydroxyphenyl)-1-piperazinyl]phenyl]carbamicAcidPhenylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1C2=CC=C(C=C2)NC(=O)OC3=CC=CC=C3)C4=CC=C(C=C4)O
• Uses: PHENYL {4-[4-(4-HYDROXYPHENYL)PIPERAZIN-1-YL]PHENYL}CARBAMATE is a carboxylic acid ester organic substance and can be used as a pharmaceutical intermediate. [4-[4-(4-Hydroxyphenyl)-1-piperazinyl]phenyl]carbamic Acid Phenyl Ester is an impurity of Posaconazole (P689600), which is orally active antifungal triazole.

Technology Process of Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate

There total 2 articles about Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate 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: 94.6%

phenyl chloroformate (1885-14-9) + 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine (74853-08-0) → phenyl N-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)carbamate (184177-81-9)

Guidance literature:

In tetrahydrofuran; at 0 - 25 ℃; Large scale;

Reference yield:

4-amino-phenol (123-30-8) → phenyl N-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)carbamate (184177-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water monomer / 6 h / 50 - 60 °C / Large scale

2.1: sodium hydroxide / water monomer / 15 h / 50 - 60 °C / Large scale

3.1: zinc powder; ammonia hydrochloride / methanol / 5 h / 20 - 30 °C / Inert atmosphere; Large scale

4.1: tetrahydrofuran / 0.5 h / 0 - 10 °C / Autoclave; Large scale

4.2: 1 h / 0 - 10 °C / Autoclave; Large scale

With ammonia hydrochloride; sodium hydroxide; zinc powder; In tetrahydrofuran; methanol; water monomer;

Reference yield: 79.7%

phenyl N-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)carbamate (184177-81-9) + C17H28N2O3*C2H2O4 → C34H45N5O5

Guidance literature:

With triethylamine; In tetrahydrofuran; at 60 - 65 ℃; for 24h; Large scale;

upstream raw materials:

phenyl chloroformate

1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine

4-amino-phenol

Downstream raw materials:

acetic acid 4-[4-(4-phenoxycarbonylamino-phenyl)-piperazin-1-yl]-phenyl ester

2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one

4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one

posaconazote

Refernces

• 1、 Jha, Anjali,Krishnam Raju, V. R.. "An Improved Scalable Preparation of the Antifungal Posaconazole". . . Retrieved 2021/11/12.
• 2、 Lv,Zhang,Wang,Pan,Liu. "Synthesis, Crystal Structure, Anti-Bone Cancer Activity and Molecular Docking Investigations of the Heterocyclic Compound 1-((2S,3S)-2-(Benzyloxy)Pentan-3-yl) -4-(4-(4-(4-Hydroxyphenyl)Piperazin-1-yl) Phenyl)-1H-1,2,4-Triazol-5(4H)-One". . p. 1173 - 1179. Retrieved 2019/08/12.