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
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].[F:26][C:27]1[C:32]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:31][CH:30]=[CH:29][N:28]=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:36]2[CH2:37][CH2:38][CH:33]([C:32]3[C:27]([F:26])=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:34][CH2:35]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-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.
Workup
- customThe reaction product was purified by chromatography
Sources & evidence
- ORD record
- ord-5c075b1f6b7c48149230455c9f1f987c
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705505
Reaction notes
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