反应 #1135

反应方程式

pyridine

trifluoroacetic acid

→

5-(4-fluorophenyl)-3-(2-piperidinyl)pyridine

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他The solvents were removed in vacuo
2. 2
   workup.DISSOLUTIONthe crude material dissolved in ethyl acetate (50 mL)
3. 3
   workup.ADDITIONSaturated sodium carbonate solution (30 mL) was added
4. 4
   其他the organic layer separated
5. 5
   萃取The aqueous phase was extracted with two further portions of ethyl acetate (2×30 mL)
6. 6
   洗涤the combined organic extracts washed with brine (20 mL)
7. 7
   干燥dried (Na2SO4)
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue was chromatographed on silica gel with ethyl acetate

实验过程

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%. 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).

来源