4-Phenylpiperidin-4-ol → HCID 21839953, compound

HRID 725065Notes

Reaction equation

HRID 725065 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])[NH:14]2)[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:23][C:24]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl.CO>[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])[NH:14]2)[CH2:10][CH2:11][N:27]2[CH2:28][CH2:29][C:24]([OH:23])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:25][CH2:26]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 21839844HCID 21839844, compound

Product 1

HCID 21839953HCID 21839953, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

3-(3,4-dichlorophenyl)-3-(3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.75 g) was coupled to 4-hydroxy-4-phenyl-piperidine (0.34 g) as described in Example 1. After chromatography, using dichloromethane:methanol (20:1) as eluent, the free amine was converted to the hydrochloride salt, to give the title compound as a white solid (0.4 g); mp 190° C.(dec); MS: m/z=495(M+1); NMR (CDCl3): 2.02 (broad,4), 2.70 (broad,4), 4.92 (broad,1), 6.95-7.73 (m,12). Analysis for C28H28Cl2N2O2.HCl.0.5 H2O: Calculated: C, 62.17; H, 5.59; N, 5.18; Found: C, 62.01; H, 5.54; N, 4.98.

Sources & evidence

ORD record
ord-03a356d15b58459fb48ac9a54563501a
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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