Phosphorus oxychloride → 4-[(3-Benzyloxy-4-formylphenyl)butylamino]butyl acetate

HRID 85329Notes

Reaction equation

HRID 85329 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:20]=1)(=[O:8])[CH3:7].[C:33]([O-])(=[O:35])C.[Na+]>CN(C)C=O>[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:33]=[O:35])=[C:21]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:20]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 680089434-[(3-Benzyloxyphenyl)butylamino]butyl acetate

Product 1

HCID 866676074-[(3-Benzyloxy-4-formylphenyl)butylamino]butyl acetateYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 10 ml of N,N-dimethylformamide was added dropwise 1.11 g (7.24 mmol) of phosphoryl chloride over 8 minutes with stirring under ice cooling. After the mixture was stirred for 1 hour, 2.67 g (7.23 mmol) of 4-[(3-benzyloxyphenyl) butylamino]butyl acetate dissolved in 4 ml of N,N-dimethylformamide was added dropwise thereto. After stirred for 1 hour, the mixture was gradually heated and stirred at 50° C. for 3 hours and further at 70° C. for 0.5 hours. To this mixture, 20 ml of a 20% sodium acetate solution was added dropwise under cooling in an ice bath. The mixture was stirred for 1 hour and subjected to extraction with ethyl acetate. Washing was performed with a saturated sodium bicarbonate solution and then with a saturated saline solution. Drying over anhydrous sodium sulfate and concentration were performed. The residue was purified by silica gel column chromatography to give 2.14 g of a yellow oily matter (yield: 74.7%).

Workup

  1. stirringAfter the mixture was stirred for 1 hour
  2. additionwas added dropwise
  3. stirringAfter stirred for 1 hour
  4. temperaturethe mixture was gradually heated
  5. stirringstirred at 50° C. for 3 hours and further at 70° C. for 0.5 hours
  6. temperatureunder cooling in an ice bath
  7. stirringThe mixture was stirred for 1 hour
  8. extractionsubjected to extraction with ethyl acetate
  9. washWashing
  10. dry with materialDrying over anhydrous sodium sulfate and concentration
  11. customThe residue was purified by silica gel column chromatography
  12. customto give 2.14 g of a yellow oily matter (yield: 74.7%)

Sources & evidence

ORD record
ord-5d62c2bc67304da1bc63031f41fbf8c4
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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