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

온도

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 기록

ord-9658191022024fcaa3be7bfde5a532b9

출처 데이터셋

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05594011