Acetyl chloride → N,N-Diethyl-4-[3-acetoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Hydrochloride

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Reaction Steps

A solution of 0.96 g (2.3 mmol) of N,N-diethyl-4-[3-hydroxyphenyl(1-propylpiperidin-4-yl)amino]benzamide was stirred in 20 mL of CH2Cl2 and 0.17 mL of acetyl chloride was added. The mixture was stirred for 2 h. The solvent was evaporated and the residue recrystallized from 2-PrOH to give 0.7 g (62% yield) of the title compound as a white crystalline solid: mp 218-219° C. MS m/z=452 (M++H). 300 MHz 1H NMR (DMSO-d6) δ7.3 (d 2H); 7.2 (m, 1H);6.9 (d, 2H);6.7 (m, 2H);4.1 (t, 3H); 3.6 (d, 2H); 3.4 (m, 4H); 2.8 (m, 4H); 2.4(m, 2H); 2.2(s, 3H) 2.1 (d, 2H); 1.9 (m, 2H); 1.2 (t, 6H), 1.0 (t, 3H). Anal calcd. for C27H37N3O3.HCl: C, 66.45; H, 7.45; N, 8.61. Found: C, 66.07; H, 7.83; N, 8.32.

Provenance & Evidence