Fluorobenzene → 4-(4-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride

Participants

Reaction Steps

1-Acetyl-4-(4-fluorobenzoyl)piperidine. N-acetylisonipecotoyl chloride (2.00 g, 10.5 mmol) was slowly added to a stirred mixture of aluminum trichloride (2.80 g, 21.1 mmol) in fluorobenzene (10 mL). After addition was complete, the mixture was refluxed for 1 h. The mixture was poured into ice and the resulting layers were separated. The aqueous layer was extracted with CH2Cl2 (2×30 mL), the combined organic phase was dried and was concentrated under reduced pressure to afford the title compound as a pale yellow oil (1.30 g, 50%): 1H NMR (CDCl3) 1.50-1.70 (m, 1H), 1.70-2.00 (m, 3H), 2.10 (s, 3H), 2.81 (t, J=12.0 Hz, 1H), 3.15-3.30 (m, 1H), 3.40-3.55 (m, 1H), 3.90 (d, J=13.2 Hz, 1H), 4.57 (d, J=13.2 Hz, 1H), 7.14 (t, J=8.4 Hz, 2H), 7.97 (dd, J=5.7 and 8.4 Hz, 2H).

Provenance & Evidence