Triethylamine → 1-{4-[2-(4-Hydroxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-piperidine-4-carboxylic Acid Dimethylamide

HRID 564156Notes

Reaction equation

HRID 564156 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]2=[O:18])=[CH:5][CH:4]=1.[CH3:19][N:20]([CH3:29])[C:21]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22].C(N(CC)CC)C>CN(C=O)C>[CH3:19][N:20]([CH3:29])[C:21]([CH:23]1[CH2:24][CH2:25][N:26]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]3=[O:18])=[CH:5][CH:4]=2)[CH2:27][CH2:28]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 411689N,N-dimethylpiperidine-4-carboxamideHCID 580428311-[2-(4-Bromomethyl-phenyl)-ethyl]-4-hydroxy-1H-pyridin-2-one

Product 1

HCID 670074151-{4-[2-(4-Hydroxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-piperidine-4-carboxylic Acid Dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 500 mg (1.62 mmol) 1-[2-(4-bromomethyl-phenyl)-ethyl]-4-hydroxy-1H-pyridin-2-one (preparation 4) in 2.5 mL DMF is added at RT 482 mg (1.79) piperidine-4-carboxylic acid dimethylamide and 0.46 mL (3.25 mmol) triethylamine. The mixture is stirred overnight at RT and after filtration is purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

Workup

  1. filtrationafter filtration
  2. customis purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Sources & evidence

ORD record
ord-69a61a6a51794bc197137d74d0053702
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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