Piperidin-4-ol → 4-Benzyloxy-1-{2-[4-(4-hydroxy-piperidin-1-ylmethyl)-phenyl]-2-oxo-ethyl}-1H-pyridin-2-one

HRID 564194Notes

Reaction equation

HRID 564194 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=2)=[O:17])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:31]3[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]3)=[CH:20][CH:19]=2)=[O:17])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 580428824-Benzyloxy-1-[2-(4-bromomethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Product 1

HCID 580428784-Benzyloxy-1-{2-[4-(4-hydroxy-piperidin-1-ylmethyl)-phenyl]-2-oxo-ethyl}-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 400 mg (0.97 mmol) 4-benzyloxy-1-[2-(4-bromomethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 15c) in 5.0 mL of DMF is added 393 mg (3.88 mmol) 4-hydroxypiperidine. The reaction mixture is stirred 1 h at RT and is directly purified by HPLC (Waters Symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 0:100).

Workup

  1. customis directly purified by HPLC (Waters Symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 0:100)

Sources & evidence

ORD record
ord-29552c6dcfdf49d9a7ccbbb03179c1e2
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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