521284-22-0

Basic information

• Product Name: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride
• Synonyms: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride;(R)-alpha-[[[2-(4-AMinophenyl)ethyl]aMino]Methyl];(R)-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]- BenzeneMethanol HCl;(R)-2-((4-AMinophenethyl)aMino)-1-phenylethanol hydrochloride;(R)--[[[2-(4-aminophenyl)ethyl]amino]methyl]-Benzenemethanol;Mirabegron INT 3;(R) -2 - [[2- (4- aminophenyl) ethyl] amino] -1-phenylethanol hydrochloride;(1R)-2-{[2-(4-Aminophenyl)ethyl]amino}-1-phenylethanol hydrochlor ide (1:1)
• CAS NO: 521284-22-0
• Molecular Formula: C₁₆H₂₀N₂O*ClH
• Molecular Weight: 292.80374
• EINECS: 1592732-453-0
• Mol File: 521284-22-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1145 at 20℃
• Vapor Pressure: 0.015Pa at 25℃
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride(521284-22-0)
• EPA Substance Registry System: (alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]benzenemethanol hydrochloride(521284-22-0)

Safety Data

• Hazardous Substances Data: 521284-22-0(Hazardous Substances Data)

Usage

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.

Synthesis

A mixture of (100 g) (R)-2-[2’ -(4-nitrophenyl)ethyl]amino] -1 -phenylethanol monohydroch bride (prepared according to example Ib), methanol (2000 mL) and Raney Nickel (20 g, wet) was stirred under hydrogen pressure (60 psi) for 6 hrs. The reaction solution was filtered, and the filtrate was concentrated in vacuo. The residue was mixed with isopropanol (300 mL) and reaction mixture was heated to 78°C (±2). The mixture was added to toluene (900 mL). The reaction mixture was gradually cooled to 28°C (±2) and stirred at this temperature for 3 hrs. The solid obtained was filtered, washed with toluene and dried under vacuo at 48°C (±2) to obtain (R)-2-[[2-(4-aminophenyl)ethyl]-amino]- I -phenylethanol monohydrochioride.Yield: 78.1 g (86.1%); Purity by HPLC: 99.14 %.

InChI:InChI=1S/C16H20N2O.ClH/c17-15-8-6-13(7-9-15)10-11-18-12-16(19)14-4-2-1-3-5-14;/h1-9,16,18-19H,10-12,17H2;1H/t16-;/m0./s1

Upstream product

• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 
• 611-71-2 (R)-Mandelic Acid 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 
• 521284-21-9 (R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride 

Downstream Products

• 223673-61-8 (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide 

Relevant articles and documents

A new process for the preparation of (R)-2-((4-Aminophenethyl)amino)-1-phenylethanol

The present invention relates to a process for the preparation (R)-2 - ((4-aminophenethyl) amino) -1 - phenylethanol, which is an intermediate of mirabberone intermediate. A manufacturing method of a high purity and high yield amide derivative is provided to produce an amide derivative having high purity and high yield without using a specific purification process by using a zinc powder reduction catalyst.

A PROCESS FOR PREPARATION OF MIRABEGRON AND ALPHA CRYSTALLINE FORM THEREOF

An improved process for the preparation of Mirabegron of formula (I) where 4- nitrophenylethylamine of formula (III) or its acid addition salt of formula (IlIa) reacted with compound of formula (XII) in a solvent, optionally in presence of base and/or catalyst to obtain (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide of formula (XIII) followed by reducing (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide of formula (XIII) in a solvent to obtain (R)-2-[2'-(4-nitrophenyl)ethyl]amino]-l-phenylethanol of formula (XIV), optionally converting it into its acid addition salt of formula (XlVa); reducing (R)-2-[2'-(4- nitrophenyl)ethyl]amino]-l -phenylethanol of formula (XIV) or its acid addition salt of formula (XlVa) further in solvent to obtain (R)-2-[[2-(4-aminophenyl)ethyl]-amino]-l -phenylethanol of formula (XV) or its acid addition salt of formula (XVa) respectively; and reacting compound (R)- 2-[[2-(4-aminophenyl)ethyl]-amino]-l-phenylethanol of formula (XV) or its acid addition salt of compound of formula (XVa) with compound of formula (VII) in solvent, optionally in the presence of acid, and/or a catalyst to obtain Mirabegron of formula (I) which is further isolated as its a- crystalline form. The compound of formula (XIV) used in the foregoing process can also be prepared by reacting with a compound of formula (III) or acid addition salt of compound of formula (IlIa) in presence of a solvent, a catalyst and optionally in presence of a base to obtain compound of formula (XIV) optionally converting it into its acid addition salt of formula (XlVa); and the same is used in the above-referred process. The compound of formula (XV) used in the foregoing process can also be prepared by reacting a compound of formula (III) or its acid addition salt of formula (IlIa) with a compound of formula (XVI) in a solvent, optionally in presence of a base, optionally in presence of a catalyst to obtain compound of formula (XVII); and optionally isolate the compound of formula (XVII) followed by reducing the compound of formula (XVII) using reducing agent, in a solvent, optionally in presence of a base, optionally in presence of a catalyst to obtain compound of formula (XV) which is further used in the above- referred process for the preparation of Mirabegron of formula (I) and its a-crystalline form. Another additional single-pot process for preparation of Mirabegron of formula (I) is disclosed, wherein compound of formula (XV) or its acid addition salt of formula (XVa) reacted with compound of formula (XVIII) in presence of a solvent and oxidizing agent, optionally in presence of base, optionally in presence of a catalyst to obtain Mirabegron of formula (I).

PROCESS FOR THE PREPARATION OF 2-(2-AMINOTHIAZOL-4-YL)-N-[4-(2-{[(2R)-2-HYDROXY-2-PHENYL ETHYL]AMINO}ETHYL)PHENYL]ACETAMIDE MONOHYDROCHLORIDE, ITS INTERMEDIATES AND POLYMORPH THEREOF

The present invention relates to a process for the preparation of 2-(2-aminothiazol-4-yl)- N-[4-(2- {[(2R)-2-hydroxy-2-phenylethyl]amino} ethyl)phenyl]acetamide monohydrochloride compound of formula- la, its intermediates and polymorph thereof. [Formula should be inserted here]