Tetrahydrofuran → 4-hydroxy-1-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1H-pyridin-2-one

HRID 15039Notes

Reaction equation

HRID 15039 reaction equation
C1COCC1.C([O:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=2)[C:16](=[O:35])[CH:15]=1)C1C=CC=CC=1>[H][H].[Pd]>[OH:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:24][CH:25]=2)[C:16](=[O:35])[CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 247808834-benzyloxy-1-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1H-pyridin-2-one

Product 1

HCID 684300184-hydroxy-1-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1H-pyridin-2-oneYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

Into a THF (10 mL) solution of 4-benzyloxy-1-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1H-pyridin-2-one (Example 2, 130 mg, 0.32 mmol), 10% palladium-on-carbon (165 mg) was added and stirred at room temperature for 10 hours in hydrogen atmosphere. The reaction liquid was filtered, washed thoroughly with methanol, and the filtrate was concentrated under reduced pressure. THF was added to the resulting residue and the formed precipitate was recovered by filtration and dried to provide the title compound (75 mg, 74%).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. washwashed thoroughly with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTHF was added to the resulting residue
  6. filtrationthe formed precipitate was recovered by filtration
  7. customdried

Sources & evidence

ORD record
ord-e0491db91f0f4cdfb76c6bf620a3cd51
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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