Diethylamine → 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-N,N-diethyl-benzamide

Participants

Reaction Steps

To a solution of diethyl amine (1.88 mL, 18.2 mmol) in CH2ClCH2Cl (7 mL) at room temperature was added a trimethylaluminum (9.1 mL, 18.2 mmol, 2M in hexanes) dropwise. The reaction mixture was stirred at room temperature for 1 hour. A solution of of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid methyl ester (1.51 g, 3.64 mmol) in (CH2)2Cl2 (6 mL) was added and the reaction mixture was heated to reflux for 14 hours. The solution was then cooled 0° C. and sat. aqueous NaHCO3 (15 mL) was added dropwise. The mixture was filtered through celite. The celite cake was washed with CH2Cl2 (40 mL). The organic layer was separated and the aqueous layer was washed with CH2Cl2 (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography with EtOAc to afford 1.4 g (84% yield) of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-N,N-diethyl-benzamide. 1HNMR (400 MHz, CDCl3) δ 7.28-7.16 (comp, 10H), 6.84-6.80 (comp, 2H), 6.68 (dd, 1H), 3.74 (s, 3H), 3.52-3.48 (comp, 2H), 3.39 (s, 2H), 3.24-3.21 (comp, 2H), 2.47-2.42 (comp, 8H), 1.22-1.20 (comp, 3H), 1.19-1.16 (comp, 3H); MS (M+1) 457.2.

Provenance & Evidence