Water → Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate

HRID 1634635Notes

Reaction equation

HRID 1634635 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH:15][N:16]([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.O>C(O)C.Cl.[Pt]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:15][N:16]([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 962WaterHCID 69859264HCID 69859264, compound

Product 1

HCID 11345737Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionateYield 82%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4.645 g (0.0186 mol) of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)acrylate were dissolved in 225 ml of ethanol in a 1 liter glass reactor, 7,46 g of Pt/C type 18 catalyst were added (4.83% Pt and 59.70% water) and a pressure of 200 psi of H2 was applied. The mixture was left hydrogenating for 3 days, after which it was filtered through Celite® 535 and was washed with 2×40 ml of ethanol. The ethanol was then removed under vacuum, to give a residue weighing 0.72 g. The residue was suspended in 40 ml of 2N hydrochloric acid and was washed with dichloromethane. The operation continued with the acid aqueous phase which was basified with a mixture of sodium carbonate and potassium carbonate (1/1) to pH 11 and the product was extracted with 4×40 ml of dichloromethane. The pooled organic phases were dried with sodium sulfate, were filtered and were evaporated to dryness under vacuum, to give a pale yellow oil weighing 3.82 g corresponding to ethyl α-(p-methoxyphenyl)-β-(dimethylamino)propionate (Yield: 82%).

Workup

  1. filtrationafter which it was filtered through Celite® 535
  2. washwas washed with 2×40 ml of ethanol
  3. customThe ethanol was then removed under vacuum
  4. customto give a residue
  5. washwas washed with dichloromethane
  6. additionwas basified with a mixture of sodium carbonate and potassium carbonate (1/1) to pH 11
  7. extractionthe product was extracted with 4×40 ml of dichloromethane
  8. dry with materialThe pooled organic phases were dried with sodium sulfate
  9. filtrationwere filtered
  10. customwere evaporated to dryness under vacuum
  11. customto give a pale yellow oil

Sources & evidence

ORD record
ord-264a2d8b557e46fead7d50936c582797
Source dataset
uspto-grants-2003_01
Patent number
US06506941B1

Reaction notes

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