4-Piperidineethanol → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-hydroxyethyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725066Notes

Reaction equation

HRID 725066 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][CH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH2:11][N:30]2[CH2:31][CH2:32][CH:27]([CH2:26][CH2:25][OH:24])[CH2:28][CH2:29]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 739534-PiperidineethanolHCID 218397793-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218398973-[1-(3,4-Dichlorophenyl)-3-(4-(2-hydroxyethyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 64.3%

Procedure

3-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.387g) was coupled to 4-(2-hydroxy-ethyl)piperidine (0.13g) 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 the Example 8 to afford the title compound (0.178 g); mp 119°-125° C. (d); MS: m/z=461(M+1); NMR(CDCl3): 2.5-2.4(m,15), 3.1 (s,3), 3.56 (broad,2), 3.7 (broad,2), 4.7 (s,1), 6.6 (d,1, J=7.5), 6.8 (s,1), 7.13 (d,1, J=8), 7.4-7.7 (m,4). Analysis for C25H30Cl2N2O2.HCl: Calculated: C, 56.19; H, 6.03; N, 5.24; Found: C, 56.01; H, 5.77; N, 5.06.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-0362531d6fb841f7ba494bc71537dea8
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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