Step 2: 1-(4-Bromophenyl)cyclobutane-1-carboxamide (8.120 g, 31.952 mmol) was dissolved in 1-butanol (50 mL), and sodium hypochlorite (11.00% aqueous, 25.101 mL, 44.733 mmol) and sodium hydroxide (3.00 M aqueous, 29.822 mL, 89.466 mmol) were added in sequence . The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was redissolved in ethyl acetate, hydrochloric acid (4.00 M solution of 1,4-dioxane, 11.982 mL, 47.928 mmol) was added and stirred. The precipitated solid was filtered, washed with ethyl acetate and dried to give 1-(4-bromophenyl)cyclobutanamine hydrochloride (3.320 g, 39.6% yield) as a white solid.
