2-Fluoroaniline → 1-(2-Fluorophenyl)piperazine

Participants

Reaction Conditions

Reaction Steps

2-Fluoroaniline (4.0 g, 36.0 mmol) and bis-(2-chloroethyl)-amine hydrochloride (6.4 g, 36.0 mmol) were dissolved in n-butanol (40 mL) and potassium carbonate (12.0 g, 86.8 mmol) was added. The reaction mixture was heated to 100° C. for 16 h, cooled to room temperature, and concentrated under reduced pressure. The crude reaction mixture was diluted with 10% MeOH in CHCl3 and filtered. The clear filtrate was concentrated under reduced pressure to get 1-(2-fluorophenyl)piperazine (2.0 g, yield 31%), which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 9.95 (br s, 1H), 7.12-6.95 (m, 4H), 3.43 (br s, 8H). MS (ESI) m/z: Calculated for C10H13FN2: 180.11. found: 180.9 (M+H)+

Provenance & Evidence