4-(4-Fluorophenyl)piperidine → HCID 18723459, compound

Participants

Reaction Steps

To a solution of 1.46 g (5.6 mmol) of 1-benzyl-3-(RS)-formyl-4-(RS)-trifluoromethylpyrrolidine and 0.13 g (0.67 mmol) of 4-(4-fluorophenyl) piperidine (Example 1, Step 1) in 30 mL of dichloroethane at rt was added 2.37 g (11.2 mmol) of sodium triacetoxyborohydride. After stirring for 18 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, acetone:hexanes, 1:8) to give 1.98 g of the title compound. 1H NMR (key peaks) (CDCl3) δ7.28-7.37 (m, 5H), 7.19-7.22 (m, 2H), 7.01 (t, 2H, J=8.5 Hz); Mass Spectrum (ESI) m/e=421 (M+1).

Provenance & Evidence