반응 #1056042

반응 방정식

3-(4-methoxyphenyl)propionic acid

propylamine hydrochloride

triethylamine

→

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

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   세척The mixture was washed with 1N hydrochloric acid, 2N sodium hydroxide, water, brine
2. 2
   기타dried
3. 3
   기타Evaporation of the solvent
4. 4
   기타yielded the pure product (10.36 g; 95.4%)

실험 절차

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).

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