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Tetrahydrofuran → 5-benzyloxy-2-(N,N-dimethylamino)methyl-4-pyridone

HRID 5512
Notes
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Reaction equation

HRID 5512 reaction equation
Cl[CH2:2][C:3]1[CH2:8][C:7](=[O:9])[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][N:4]=1.O1CCCC1.Cl.[CH3:24][NH:25][CH3:26].[OH-].[Na+]>O>[CH2:11]([O:10][C:6]1[C:7](=[O:9])[CH2:8][C:3]([CH2:2][N:25]([CH3:26])[CH3:24])=[N:4][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 677480612-Chloromethyl-5-benzyloxy-4-pyridone

Product 1

HCID 677480495-benzyloxy-2-(N,N-dimethylamino)methyl-4-pyridoneYield 96.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixture of 2-chloromethyl-5-benzyloxy-4-pyridone (1.0 g), tetrahydrofuran (10 ml) and water (10 ml) were added dimethylamine hydrochloride (1.31 g) and sodium hydroxide (0.64 g). After being stirred for 1.5 hours, the mixture was concentrated under reduced pressure to dryness. The residue was dissolved in methanol and the insoluble material was filtered off. The filtrate was evaporated in vacuo to give 5-benzyloxy-2-(N,N-dimethylamino)methyl-4-pyridone (1.0 g) as a powder.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure to dryness
  2. dissolutionThe residue was dissolved in methanol
  3. filtrationthe insoluble material was filtered off
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5543a960e72d4b11830530e7308453a5
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244890

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes