1,2-Dichloroethane → HCID 178520485, compound

Participants

Reaction Steps

A mixture of 3-(4-hydroxyphenyl)propionic acid 7 (0.48 g, 2.9 mmol), amine 5 (0.50 g, 2.9 mmol), EDC (0.67 g, 3.5 mmol), and HOBT (0.39 g, 2.9 mmol) in DMF (5 mL) was stirred under an atmosphere of nitrogen overnight. The reaction mixture was partitioned between H2O (25 mL) and EtOAc (50 mL). The organic layer was washed with H2O, 3N HCl (25 mL), H2O (25 mL), and saturated NaCl (25 mL). After drying (Na2SO4), concentration under reduced pressure gave (a) trans-3-(4-hydroxyphenyl)-N-(4-phenylcyclohexyl)propionamide (0.65 g, 69%) which was used without further purification: 1H NMR (300 MHz, CD3OD) δ 7.28-7.06 (m, 5H), 3.74-3.60 (m, 1H), 2.80 (t, J=4 Hz, 2H), 2.51-2.36 (m, 3H), 1.97-1.82 (m, 4H), 1.67-1.51 (m, 2H), 1.40-1.21 (m, 2H).

Provenance & Evidence