4-Phenylpiperidin-4-ol → HCID 21839807, compound

HRID 1738952Notes

Reaction equation

HRID 1738952 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]=[C:19]([F:22])[CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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]=[C:19]([F:22])[CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH2:11][N:29]2[CH2:30][CH2:31][C:26]([OH:25])([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:27][CH2:28]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 21839919HCID 21839919, compound

Product 1

HCID 21839807HCID 21839807, compoundYield 129.9%

Procedure

3-(3,4-Dichlorophenyl)-3-(6-fluoro-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (2.05 g) was coupled to 4-hydroxy-4-phenylpiperidine (1.0 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 (2.05 g); mp 160-205° C.; MS: m/z=527(M+1); NMR(CD3SOCD3): 1.78 (m,2), 2.17 (m,1), 3.12 (s,3), 4.89 (m,1), 6.88 (d,1, J=8.3), 7.10-7.59 (m,9), 7.84 (d,1, J=8.7). Analysis for C29H29Cl2N2O2F.1.0 HCl.1.0 H2O: Calculated: C, 59.85; H, 5.54, N, 4.81; Found: C, 60.15; H, 5.39; N, 4.81.

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-6042cbcd009c4a4eb99a6b85a48b5911
Source dataset
uspto-grants-1999_10
Patent number
US05965576

Reaction notes

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