Pyridine → 5-(4-Fluorophenyl)-3-(2-piperidinyl)pyridine

Temperatur

25 °C

The above-described pyridine derivative (1.25 g, 3.5 mmol) was dissolved in a mixture of dichloromethane (10 mL) and trifluoroacetic acid (10 mL) and this was stirred at 25° C. for 18 h. The solvents were removed in vacuo and the crude material dissolved in ethyl acetate (50 mL). Saturated sodium carbonate solution (30 mL) was added and the organic layer separated. The aqueous phase was extracted with two further portions of ethyl acetate (2×30 mL), the combined organic extracts washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel with ethyl acetate, then methanol:ethyl acetate (1:9) as eluant to afford 5-(4-fluorophenyl)-3-(2-piperidinyl)pyridine, 940 mg, 100%. 1H NMR (CDCl3, 300 MHz): δ 8.69 (d, J=2 Hz, 1 H), 8.55 (d, J=2 Hz, 1 H), 7.93 (t, J=2 Hz, 1 H), 7.56 (m, 2 H), 7.16 (app. tm, J=9 Hz, 2 H), 3.18 (d, J=12 Hz, 1 H), 2.83 (td, J=12, 3 Hz, 1 H), 2.61 (bs exch., 1 H), 1.92 (m, 2 H), 1.45-1.75 (m, 6 H).

1. customThe solvents were removed in vacuo
2. dissolutionthe crude material dissolved in ethyl acetate (50 mL)
3. additionSaturated sodium carbonate solution (30 mL) was added
4. customthe organic layer separated
5. extractionThe aqueous phase was extracted with two further portions of ethyl acetate (2×30 mL)
6. washthe combined organic extracts washed with brine (20 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed on silica gel with ethyl acetate

ORD-Eintrag

ord-ed9a8965e87f4065b53ebdd07a1747f1

Quelldatensatz

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05677459