4-Phenylpiperidin-4-ol → HCID 19711216, compound

HRID 725082Notes

Reaction equation

HRID 725082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([O:22][CH3:23])[CH:18]=[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].[OH:26][C:27]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[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](=[C:17]([O:22][CH3:23])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:24])[N:14]2[CH3:25])[CH2:10][CH2:11][N:30]2[CH2:31][CH2:32][C:27]([OH:26])([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:28][CH2:29]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 21839858HCID 21839858, compound

Product 1

HCID 19711216HCID 19711216, compoundYield 115.9%

Procedure

3-(3,4-Dichlorophenyl)-3-(4-methoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.95 g) was coupled to 4-hydroxy-4-phenylpiperidine (0.44 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 (0.838 g); mp 163°-185° C.; MS: m/z=539(M+1); NMR(CD3SOCD3): 1.78 (m,2), 2.10 (m,1), 2.98-3.22 (two peaks,3), 3.77 (s,3), 4.77 (m,1), 5.45 (m,1) 6.69-7.58 (m,11). Analysis for C30H32Cl2N3O2.1.0.HCl.1.0H2O: Calculated: C, 60.66; H, 5.94, N, 4.71; Found: C, 60.67; H, 5.94; N, 4.71.

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-5fc5e0944b8749fa81ce992895b9a2f0
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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