2-(Benzylamino)-1-(4-methoxyphenyl)-propane Chemical Properties

Boiling point:

377.8±22.0 °C(Predicted)

Density 

1.024±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Miscible with methanol, Methylene chloride. Immiscible with water

pka

9.54±0.19(Predicted)

form 

Oil

color 

Pale yellow to yellow liquid

InChI

InChI=1S/C17H21NO/c1-14(18-13-16-6-4-3-5-7-16)12-15-8-10-17(19-2)11-9-15/h3-11,14,18H,12-13H2,1-2H3

InChIKey

CVGPWMGXKOKNFD-UHFFFAOYSA-N

SMILES

C(C1=CC=C(OC)C=C1)C(NCC1=CC=CC=C1)C

LogP

4.8

CAS DataBase Reference

43229-65-8(CAS DataBase Reference)

2-(Benzylamino)-1-(4-methoxyphenyl)-propane Usage And Synthesis

Chemical Properties

Pale yellow liquid

Uses

1-(4-Methoxyphenyl)-2-(benzylamino)propane is an intermediate in the synthesis of Formoterol Fumarate (F693401).

Synthesis

GENERAL METHOD: 1-(4-methoxyphenyl)propan-2-one (8.22 g, 50.0 mmol) and benzylamine (5.35 g, 50.0 mmol) were dissolved in methanol and 5% Pt/C catalyst (0.83 g) was added. The reaction mixture was stirred at 60°C and hydrogenated for 24 hours. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was removed by rotary evaporation to afford the intermediate N-benzyl-1-(4-methoxyphenyl)propan-2-amine in 95% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.25 (ddd, J = 16.5, 11.1, 6.8 Hz, 5H), 7.07 (d, J = 8.5 Hz, 2H), 6.83 (d, J = 8.5 Hz, 2H), 3.86 (d, J = 13.3 Hz, 1H), 3.79 (s, 3H), 3.73 (d, J = 13.3 Hz, 1H), 2.90 (dd, J = 13.0, 6.5 Hz, 1H), 2.71 (dd, J = 13.5, 7.1 Hz, 1H), 2.61 (dd, J = 13.5, 6.4 Hz, 1H), 1.10 (d, J = 6.2 Hz, 3H). lc/ms (ESI m/z): 256.4 ( M + H)+.

References

[1] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1125 - 1128
[2] Organic Process Research and Development, 1998, vol. 2, # 2, p. 96 - 99
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2903 - 2915
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[5] Patent: US2011/313199, 2011, A1. Location in patent: Page/Page column 14

2-(Benzylamino)-1-(4-methoxyphenyl)-propane(43229-65-8)Related Product Information

• Trimethoprim
• Diethylstilbestrol
• Benzyl benzoate
• Phenoxybenzamine hydrochloride
• Benzyl alcohol
• 4-Fluorobenzylamine
• Benzyl bromide
• Formoterol Fumarate Dihydrate EP Impurity I
• Formoterol Impurity 13
• n-benzyl-m-toluidine
• N-METHYL-N-BENZYLANILINE
• N-Phenylbenzylamine
• 2-PHENYLBENZYLAMINE HYDROCHLORIDE
• N-Benzyl-N-ethylaniline
• 1-(4-Methoxyphenyl)-2-benzylaminopropane
• Methoxy