4-Piperidin-4-ylphenol → 3-[1-(3,4-Dichlorophenyl)-3-(4-(4-hydroxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

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Reaction Steps

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.378 g) was coupled to 4-(4-hydroxy-phenyl)piperidine (0.191 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the corresponding hydrochloride salt as described in Example 8 to afford the title compound (0.414 g); mp 150°-160° C.; MS: m/z=508(M+1); NMR(CD3SOCD3): 1.93-2.06 (m,4), 2.65-2.73 (m,3), 3.06 (s,3), 3.35 (m,4), 3.6-3.7 (m,3), 4.87 (d,1, J=3.5), 6.7-6.8 (m,3), 6.9-7.0 (m,3), 7.32 (d,1, J=8.3), 7.50 (s,2), 7.64 (m,1), 7.95 (d,1, J=7.7). Analysis for C29H30Cl2N2O2.1.0 HCl.1.0 H2O: Calculated: C, 61.87; H, 5.73; Found: C, 62.13; H, 5.94.

Provenance & Evidence