Azanium;hydrate → 5-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-4(1H)-one

HRID 385601Notes

Reaction equation

HRID 385601 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:19])[CH:7]=[C:8]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)O[CH:10]=1.O.[NH4+:21]>C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:19])[CH:7]=[C:8]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[NH:21][CH:10]=1

Participants

4

Reactant 2

HCID 22024077Azanium;hydrateHCID 578152005-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one

Product 1

HCID 578154885-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.2 g of 5-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one in 5 mL of ethanol, 16 mL of 25% ammonium water was added, and the mixture was heated under reflux while stirring for 9 hours 30 minutes. The solvent was distilled off under reduced pressure, and the resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=95:5 to 90:10 to obtain 0.42 g of 5-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-4(1H)-one as a brown oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resultant residue was purified by flash silica gel column chromatography
  5. washelution with chloroform

Sources & evidence

ORD record
ord-555535f27b1649bfa8aaf16821f48114
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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