4-(2-Methoxyphenyl)piperidine → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methoxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

Participants

Reaction Steps

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.368 g) was coupled to 4-(2-methoxyphenyl)piperidine (0.203 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 desired title compound (0.469 g); mp 175°-182° C.; MS: m/z=523(M+1); NMR(CD3SOCD3): 1.83-1.90 (m,3), 2.05-2.13 (m,2), 2.80 m(1), 3.07 (s,3), 3.57 (m,2), 3.8 (s,3), 4.89 (d,1, J=3.7), 6.7 (dd,1, J=8.4, 2), 7.0 (m,3), 7.12-7.6 (m,6), 7.94 (d,1, J=7.5). Analysis for C30H32Cl2N2O2.1.0 HCl.1.5 H2O: Calculated: C, 61.39; H, 6.18, N, 4.77; Found: C, 61.33; H, 6.12; N, 4.99.

Provenance & Evidence