BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)- Chemical Properties

Melting point:

97-100°C

Boiling point:

447.9±24.0 °C(Predicted)

Density 

1.137±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)

pka

13.98±0.20(Predicted)

form 

Solid

color 

Off-White to Light Beige

InChI

InChI=1/C16H20N2O/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/t16-/s3

InChIKey

TUAHDMSPHZSMQN-QEIABERDNA-N

SMILES

[C@@H](O)(C1=CC=CC=C1)CNCCC1=CC=C(N)C=C1 |&1:0,r|

BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)- Usage And Synthesis

Uses

(R)-2-((4-Aminophenethyl)amino)-1-phenylethanol is an intermediate in the synthesis of Mirabegron related compounds. irabegron is a potent bladder relaxant and reagent for diabetes remedy.

Synthesis

(R)-2-((4-nitrophenylethyl)amino)-1-phenylethanol hydrochloride (Compound I, 15 g, 0.0465 mol) was dissolved in 150 mL of methanol with stirring. Ammonium formate (14.6 g, 0.2325 mol) and 1.5 g of 10% palladium carbon catalyst were subsequently added. The reaction mixture was heated to 65 °C and kept at reflux for 5 hours. The reaction was monitored by thin layer chromatography (TLC, GF254 plate, unfolding agent ratio ethyl acetate:methanol = 5:1) until the fluorescent spots of compound I disappeared. Upon completion of the reaction, methanol was removed by concentration under reduced pressure, followed by the addition of water and ethyl acetate for extraction. The organic phase was evaporated under reduced pressure to remove ethyl acetate to give an off-white solid product (Compound II, 10.91 g) in 91.71% yield.

References

[1] Patent: CN105481705, 2016, A. Location in patent: Paragraph 0021; 0022; 0023
[2] Patent: WO2014/132270, 2014, A2. Location in patent: Page/Page column 19

BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-(391901-45-4)Related Product Information

• (R)-2-(2-aminothiazol-4-yl)-N-(2-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide
• Mirabegron Impurity
• Mirabegron Impurity 33
• Mirabegron Impurity 38
• 2-[[2-2(2-Amino-4-thiazolyl)acetyl]amino]-4-thiazoleacetic Acid
• Mirabegron Impurity 8 HCl
• Mirabegron 2-Oxo Impurity
• Mirabegron iMpurity
• (alphaR)-alpha-[[[2-(4-Nitrophenyl)ethyl]amino]methyl]benzenemethanol
• Mirabegron Impurity 34