4-Piperidin-4-ylphenol → 3-[1-(3,4-Dichlorophenyl)-3-(4-(4-hydroxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 1082200Notes

Reaction equation

HRID 1082200 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH2:11][N:34]2[CH2:33][CH2:32][CH:31]([C:28]3[CH:29]=[CH:30][C:25]([OH:24])=[CH:26][CH:27]=3)[CH2:36][CH2:35]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 105115114-Piperidin-4-ylphenolHCID 218397793-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218398203-[1-(3,4-Dichlorophenyl)-3-(4-(4-hydroxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 139.7%

Procedure

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.378 g) was coupled to 4-(4-hydroxy-phenyl)piperidine (0.191 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 title compound (0.414 g); mp 150°-160° C.; MS: m/z=508(M+1); NMR(CD3SOCD3): 1.93-2.06 (m,4), 2.65-2.73 (m,3), 3.06 (s,3), 3.35 (m,4), 3.6-3.7 (m,3), 4.87 (d,1, J=3.5), 6.7-6.8 (m,3), 6.9-7.0 (m,3), 7.32 (d,1, J=8.3), 7.50 (s,2), 7.64 (m,1), 7.95 (d,1, J=7.7). Analysis for C29H30Cl2N2O2.1.0 HCl.1.0 H2O: Calculated: C, 61.87; H, 5.73; Found: C, 62.13; H, 5.94.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-5f71c5e3018d46ccb4f1e747dcc1a7ef
Source dataset
uspto-grants-1996_12
Patent number
US05589489

Reaction notes

Loading…