3-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxopiperidino)piperidino)propyl]-2-ethyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725110Notes

Reaction equation

HRID 725110 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[CH2:23][CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:25]=[C:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]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[CH2:23][CH3:24])[CH2:10][CH2:11][N:35]2[CH2:34][CH2:33][CH:32]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][C:26]3=[O:25])[CH2:37][CH2:36]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 218397513-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehydeHCID 21839852[1,4'-Bipiperidin]-2-one

Product 1

HCID 218399963-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxopiperidino)piperidino)propyl]-2-ethyl-2,3-dihydroisoindol-1-one hydrochlorideYield 137.4%

Procedure

A solution of 3-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.476 g) was treated with 4-(2-oxopiperidino)piperidine (0.945 g) as described in Example 8. The resulting material was not purified by chromatography but was transformed into the hydrochloride to give title compound (0.51 g); mp 135°-140° C. (dec); MS: m/z=558(M+1); NMR(CD3OD): 1.22 (m,3), 2.2 (m,12), 3.0 (m,11), 4.5 (m, 1), 5.04 (d,1, J=3.85), 7.27 (m,7). Analysis for C29H35Cl2N3O2. HCl.H2O: Calculated: C, 59.74; H, 6.56; N, 7.20; Found: C, 59.77; H, 6.33; N, 6.83.

Workup

  1. customThe resulting material was not purified by chromatography

Sources & evidence

ORD record
ord-61ca7918977f465683899a2307c6ce67
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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