Fluorobenzene → 1-Acetyl-4-(4-fluorobenzoyl)piperidine

Beteiligte Stoffe

Reaktionsschritte

N-acetyl-isonipecotic acid chloride (2.0 g, 10.5 mmol) was slowly added to a stirring mixture of aluminum trichloride (2.8 g, 21.1 mmol) in fluorobenzene (10 mL). After the addition was completed, the mixture was refluxed for 1 h. The mixture was poured into ice and the resulting layers were separated. The aqueous layer was extracted twice with CH2Cl2 (2×30 mL) and the combined organic phase was dried and concentrated under reduced pressure to afford the title compound as an oil (1.3 g, 50%). 1H NMR (CDCl3): 1.5-1.7 (m, 1H), 1.7-2.0 (m, 3H), 2.104 (s, 3H), 2.813 (t, J=12.0 Hz, 1H), 3.15-3.3 (m, 1H), 3.4-3.55 (m, 1H), 3.902 (d, J=13.2 Hz, 1H), 4.574 (d, J=13.2 Hz, 1H), 7.145 (t, J=8.4 Hz, 2H), 7.967 (dd, J=5.7 & 8.4 Hz, 2H).

Herkunft & Nachweise