4-Phenylpiperidin-4-ol → 3-[1-(3,4-Dichlorophenyl)-3-(4-hydroxy-4-phenylpiperidino)propyl]-6-methoxy-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

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Reaction Steps

3-(3,4-Dichlorophenyl)-3-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.59 g) was coupled to 4-hydroxy-4-phenylpiperidine (0.27 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 (0.26 g); mp 154°-180° C. (d); MS: m/z=539(M+1); NMR(CD3SOCD3): 1.73-1.77 (m,2), 2.0 (m,1), 3.79 (two peaks,3), 5.46 (d,1, J=9.5), 6.98 (d,1, J=8), 7.03 (m,2), 7.17-7.58 (m,7), 7.82 (d,1, J=8). Analysis for C30H32Cl2N2O3.2.0 HCl: Calculated: C, 58.83; H, 5.59, N, 4.57; Found: C, 58.39; H, 5.60; N, 4.66.

Provenance & Evidence