3-(Piperidin-4-yl)pyridine → (3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-pyrid-3-ylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

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Reaction Steps

A solution of (3S)-3-(3,4-dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.428 g) was treated with 4-pyrid-3-ylpiperidine (0.20 g) as described in Example 8. The resulting material was not purified by chromatography, but was transformed into the hydrochloride to afford the title compound (0.535 g); [α]D =34° (c=1.0 ethanol); mp 170°-210° C. (dec); MS: m/z=494(M+1); NMR: 2.12 (m,4), 3.03 (s,3), 3.69 (m,7), 4.88 (m,1), 6.75 (m,1), 6.96 (m,1), 7.32 (m,1), 7.49 (m,2), 7.63(m,1), 7.92 (m,2), 8.37 (m,1), 8.81 (m,2). Analysis for C28H29Cl2N3O.2 HCl.H2O: Calculated C, 57.45; H, 5.68; N, 7.18; Found: C, 57.22; H, 5.67; N, 7.12.

Provenance & Evidence