N-(4-Phenylpiperidin-4-yl)acetamide → 3-[1-Methyl-1-(3,4-dichlorophenyl)-3-(4-acetamido-4-phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

Participants

Reaction Steps

3-Methyl-3-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (isomer A described below) (0.35 g) was coupled to 4-acetamido-4-phenylpiperidine (0.25 g) by a method similar to that described in Example 8. The reaction product was purified by chromatography and converted to the corresponding hydrochloride salt as described in the Example 8 to afford the title compound (0.354 g); mp 195°-225° C.; MS: m/z=564(M+1); NMR(CDCl3): 1.0 (s,3), 1.91 (s,1), 2.50 (s,3), 2.98 (m,4), 3.37 (m,2), 7.22-7.72 (m,10), 7.79 (s,1), 8.13 (s,1). Analysis for C32H35Cl2N3 O2.1.0 HCl.2.0 H2O: Calculated: C, 60.33; H, 6.33, N, 6.59; Found: C, 60.09; H, 5.97; N, 6.28.

Provenance & Evidence