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-methoxy-3-pyridyl)piperidino)propyl]-6-methoxy-2-methyl-2,3-dihydroisoindol-1-one hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15](=[O:24])[N:14]2[CH3:25])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:26][O:27][C:28]1[C:33]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:32][CH:31]=[CH:30][N:29]=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15](=[O:24])[N:14]2[CH3:25])[CH2:10][CH2:11][N:37]2[CH2:38][CH2:39][CH:34]([C:33]3[C:28]([O:27][CH3:26])=[N:29][CH:30]=[CH:31][CH:32]=3)[CH2:35][CH2:36]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 2
Product 1
Procedure
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-methoxy-3-pyridyl)piperidine (0.60 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 desired title compound (0.26 g); mp 135°-194° C. (d); MS: m/z=554(M+1); NMR(CD3OD): 1.9-2.1 (m,4), 2.6 (m,2), 2.9-3.1 (m,8), 3.6-3.8 (m,4), 3.8 (s,3), 4.0 (s,3), 4.8 (d,1, J=4), 6.7-8.1 (m,9). Analysis for C30H33 Cl2N3O3.1.5 HCl.0.5 H2O: Calculated: C, 58.29; H, 5.79, N, 6.80; Found: C, 58.25; H, 5.71; N, 6.68.
Workup
- customThe reaction product was purified by chromatography
Sources & evidence
- ORD record
- ord-637d34dfac89443bbd46570bb6d31e51
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705505
Reaction notes
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