反应 #217928

反应方程式

sodium borohydride

6-(4-Piperidin-3-yl-phenoxy)-nicotinamide

(±)-6-(4-Piperidin-3-yl-phenoxy)-nicotinamide hydrochloride

compound

(±)-6-(4-Piperidin-3-yl-phenoxy)-nicotinamide hydrochloride

cyclohexanecarboxaldehyde

→

title compound

收率 19.0%

(±)-6-[4-(1-Cyclohexylmethyl-piperidin-3-yl)-phenoxy]-nicotinamide

收率 19.0%

反应条件

后处理

1. 1
   浓缩concentrate
2. 2
   其他purify by silica gel chromatography (20:1→10:1 ethyl acetate:methanol)

实验过程

Combine 6-(4-Piperidin-3-yl-phenoxy)-nicotinamide (free base of compound of example 322) (0.96 mL of 0.12 M stock solution in methanol, 0.0344 g, 0.116 mmol) and cyclohexanecarboxaldehyde (0.021 mL, 0.173 mmol), and stir overnight. Add sodium borohydride (0.0108 g, 0.285 mmol), stir for 4.5 h, then concentrate and purify by silica gel chromatography (20:1→10:1 ethyl acetate:methanol) to provide 0.0085 g (19%) of the title compound as a white solid: high resolution mass spectrum (electrospray): m/z calc for C24H32N3O2 394.2495, found 394.2488; 1H NMR (CDCl3): 8.58 (s, 1H), 8.14 (d, 1H, J=7.8 Hz), 7.27 (d, 2H, J=8.3 Hz), 7.05 (d, 2H, J=7.8 Hz), 6.93 (d, 1H, J=8.8 Hz), 5.89 (s br, 2H), 2.99-2.77 (m, 3H), 2.16-2.06 (m, 2H), 1.97-1.83 (m, 3H), 1.80-1.59 (m, 7H), 1.54-1.34 (m, 2H), 1.29-1.03 (m, 5H), 0.93-0.77 (m, 3H).

来源