反应详情

To a solution of 1-(2,6-dichloro-3-nitro-benzyl)-piperidine (21) (0.894 g, 3.09 mmol) and triethylamine (0.606 g, 6 mmol) in anhydrous THF (5 mL), p-methoxy benzylamine (0.823 g, 6 mmol) was added at 0° C. under stirring. The reaction mixture was allowed to warm to room temperature and stirred for additional 12 hours and evaporated to dryness. The product was extracted with EtOAc (100 mL) and washed with water (2×50 mL) and dried (MgSO4). The product was purified by column chromatography (SiO2, hexanes:EtOAc, 95:5 to 9:1) as a yellow oil. Yield: 0.81 g, 67%. 1H-NMR (CDCl3) δ 1.23-1.26 (m, 6H), 2.23 (m, 4H), 3.63 (s, 2H), 3.76 (s, 3H), 3.92 (d, 2H, J=4.4 Hz), 6.65 (d, 1H, J=9.04 Hz), 6.82 (d, 2H, J=8.6 Hz), 7.18 (d, 2H, J=8.6 Hz), 7.18 (d, 2H, J=8.6 Hz) 7.57 (d, 1H, J=9 Hz), 8.29 (bs, 1H). NOE's were observed from H4 to H3, H5, H6. No NOE was observed from H4 to H1, which would have been expected if the other regioisomer was formed. MS (CI) m/z 390 (M+1), 392 (M+2).

1. stirringstirred for additional 12 hours
2. customevaporated to dryness
3. extractionThe product was extracted with EtOAc (100 mL)
4. washwashed with water (2×50 mL)
5. dry with materialdried (MgSO4)
6. customThe product was purified by column chromatography (SiO2, hexanes:EtOAc, 95:5 to 9:1) as a yellow oil
7. customwas formed