Propylamine → HCID 10332696, compound

HRID 1165170Notes

Reaction equation

HRID 1165170 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]([O:12][C:13]1[C:18](=[O:19])[CH:17]=[CH:16]O[C:14]=1[CH3:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[CH2:5]([O:12][C:13]1[C:18](=[O:19])[CH:17]=[CH:16][N:4]([CH2:1][CH2:2][CH3:3])[C:14]=1[CH3:20])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 10332696HCID 10332696, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The starting material can be prepared as follows: 20.64 ml of n-propylamine are added to a solution of 43.24 g of 3-benzyloxy-2-methyl-4H-pyran-4-one in 1000 ml of methanol, followed by the addition of 12.0 g of sodium hydroxide in 100 ml of methanol. The reaction mixture is refluxed for 3 hours, then concentrated by evaporation. The residue is taken up in methylene chloride and the organic solution is washed with water. The phases are clarified by addition of a saturated solution of sodium chloride in water, and the organic extract is dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue is dried under a high vacuum, giving 3-benzyloxy-2-methyl-1-n-propyl-4(1H)-pyridinone as an oily product.

Workup

  1. customThe starting material can be prepared
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. concentrationconcentrated by evaporation
  4. washthe organic solution is washed with water
  5. additionThe phases are clarified by addition of a saturated solution of sodium chloride in water
  6. extractionthe organic extract
  7. dry with materialis dried over sodium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residue is dried under a high vacuum

Sources & evidence

ORD record
ord-c2f1925e1ed34d5da646bce54b7947a9
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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