Reacción #1056042

Ecuación de reacción

3-(4-methoxyphenyl)propionic acid

propylamine hydrochloride

triethylamine

→

3-(4-Methoxy-phenyl)-N-propyl-propionamide

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe mixture was washed with 1N hydrochloric acid, 2N sodium hydroxide, water, brine
2. 2
   Otrodried
3. 3
   OtroEvaporation of the solvent
4. 4
   Otroyielded the pure product (10.36 g; 95.4%)

Procedimiento

To a solution of 3-(4-methoxyphenyl)propionic acid (8.0 g, 44.4 mmol), propylamine hydrochloride (4.24 g, 44.4 mmol), 4-dimethylaminopyridine (0.65 g, 5.33 mmol) and triethylamine (6.9 mL, 48.96 mmol) in methylene chloride (70 mL) was added 1-[(3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (10.21 g, 53.28 mmol). The reaction mixture was stirred overnight at ambient temperature followed by dilution with methylene chloride. The mixture was washed with 1N hydrochloric acid, 2N sodium hydroxide, water, brine and dried. Evaporation of the solvent yielded the pure product (10.36 g; 95.4%): 1HNMR (400 MHz, CDCl3) δ 7.76 (brs, 1H), 7.10 (d, 2H, J=8.8 Hz), 6.79 (d, 2H, J=8.0 Hz), 3.68 (s, 3H), 2.95 (q, 2H, J=5.6 Hz). 2.71 (t, 2H, J=7.6 Hz), 2.28 (t, 2H, J=7.2 Hz), 1.34 (m, 2H), 0.77 (t, 3H, J=7.2 Hz); ESMS m/z (relative intensity) 222.2 (M+H+, 100).

Fuente