3-(3,4-Dichlorophenyl)-3-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-fluoro-3-pyridyl)piperidino)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 (0.38 g) was coupled to 4-(2-fluoro-3-pyridyl)piperidine (0.47 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 (0.25 g); mp 99°-148° C. (d); MS: m/z=542(M+1); NMR(CD3OD) : 2.1 (m,4), 2.5-2.6 (m,2), 2.9 (m,1), 3.1-3.2 (m,5), 3.6-3.8 (m,6), 4.8 (d, 1, J=4), 6.7-7.5 (m,6), 7.8-8.1 (m,3). Analysis for C28H30 Cl2N3O2F.HCl.H2O: Calculated: C, 58.35; H, 5.57, N, 7.04; Found: C, 57.99; H, 5.47; N, 7.18.

Provenance & Evidence