(1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochloride

Base Information

• Chemical Name: (1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochloride
• CAS No.: 521284-22-0
• Molecular Formula: C16H20N2O^.ClH
• Molecular Weight: 292.809
• European Community (EC) Number: 700-425-8
• Mol file: 521284-22-0.mol

Synonyms:2-[2-(4-aminophenyl)ethylamino]-1-phenylethanol;1624261-01-3;Mirabegron Impurity 27 (S- Isomer of impurity of stage III);(1R)-2-{[2-(4-AMINOPHENYL)ETHYL]AMINO}-1-PHENYLETHANOL HYDROCHLORIDE;Mirabegron Impurity 6;SCHEMBL16596122;DA-21175

Chemical Property of (1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochloride

Chemical Property:

• Vapor Pressure: 0.015Pa at 25℃
• PSA: 58.28000
• Density: 1145 at 20℃
• LogP: 3.90860
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 256.157563266
• Heavy Atom Count: 19
• Complexity: 233

Purity/Quality:

>98% ^*data from raw suppliers

(R)-2-((4-Aminophenethyl)amino)-1-phenylethanolHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CNCCC2=CC=C(C=C2)N)O
• Uses: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

Technology Process of (1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochloride

There total 4 articles about (1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochloride 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: 93.0%

(R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride (521284-21-9) → (R)-2-[ [2-(4-aminophenyl)ethyl]-amino]-1-phenylethanol monohydrochloride (521284-22-0)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 1h; Reagent/catalyst; Time;

Reference yield:

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (R)-2-[ [2-(4-aminophenyl)ethyl]-amino]-1-phenylethanol monohydrochloride (521284-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Trimethyl borate; N-ethyl-N,N-diisopropylamine / acetonitrile / 8 h / Reflux

2.1: sodium tetrahydroborate / tetrahydrofuran / 25 °C

2.2: 11 h / 0 - 20 °C / Reflux

2.3: 20 - 25 °C

3.1: hydrogen / methanol / 2 h / 20 °C

With sodium tetrahydroborate; Trimethyl borate; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/acs.oprd.9b00365

Reference yield:

(R)-Mandelic Acid (611-71-2) → (R)-2-[ [2-(4-aminophenyl)ethyl]-amino]-1-phenylethanol monohydrochloride (521284-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Trimethyl borate; N-ethyl-N,N-diisopropylamine / acetonitrile / 8 h / Reflux

2.1: sodium tetrahydroborate / tetrahydrofuran / 25 °C

2.2: 11 h / 0 - 20 °C / Reflux

2.3: 20 - 25 °C

3.1: hydrogen / methanol / 2 h / 20 °C

With sodium tetrahydroborate; Trimethyl borate; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/acs.oprd.9b00365

upstream raw materials:

(R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride

2-(4-nitrophenyl)ethylamine monohydrochloride

(R)-Mandelic Acid

(2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide

Downstream raw materials:

(R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide

Refernces

• 1、 Bangal, Mukund N.,Deshmukh, Dattatray G.,Kalawade, Kaustubh A.,Mathad, Vijayavitthal T.. "Systematic Investigation into the Formation of Significant Amounts of Unknown Impurity during Scale-up of NaBH4-I2 Mediated Reduction of Nitro-Amide Intermediate of Mirabegron No.". . p. 286 - 293. Retrieved 2020/03/10.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF 2-(2-AMINOTHIAZOL-4-YL)-N-[4-(2-[[(2R)-2-HYDROXY-2- PHENYLETHYL]AMINO]-ETHYL)PHENYL]ACETAMIDE". Page/Page column 19; 20. . Retrieved 2015/11/17.