Azepane → 2,3,4,5,6,7-Hexahydro-1-(4-hydroxy-2-phenylbutanoyl)-1H-azepine

Participants

Reaction Steps

2,3,4,5,6,7-Hexahydro-1H-azepine (3.36 g, 33.9 mmol) in 1,2-dichloroethane (10 ml) was added to a cooled (ice/water) solution of triethylamine (4.68 g, 46.2 mmol) and aluminium trichloride (4.52 g, 33.9 mmol) in 1,2-dichloroethane (70 ml). A solution of 2-phenylbutyrolactone (5.00 g, 30.8 mmol) in 1,2-dichloroethane (50 ml) was added to the cooled reaction mixture and stirring continued overnight. The reaction mixture was poured into water (150 ml), basified with 2M-NaOH, and washed with ethyl acetate (3×80 ml). The combined organic phases were washed with brine (80 ml) and water (80 ml), dried (MgSO4), and concentrated in vacuo to afford a brown oil which partially solidified on standing. The crude product was chromatographed on silica gel, eluting with ethyl acetate to give the title compound as an oil (2.68 g, 33.3%).

Provenance & Evidence