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

HRID 1634636Notes

Reaction equation

HRID 1634636 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.[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

5

Reactant 2

HCID 962WaterHCID 69859264HCID 69859264, compound

Product 1

HCID 11345737Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionateYield 74%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

19.8 g (0.0795 mol) of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)acrylate were dissolved in 740 ml of ethanol, in a 1 liter glass reactor, 30.6 9 of Pt/C type 18 catalyst (4.83% Pt and 59.70% water) were added, the mixture was first purged with nitrogen and then with hydrogen and finally a pressure of 600 psi H2 was applied. The mixture was left hydrogenating for 23 hours, was then filtered through Celite® 535 and was washed with 2×165 ml of ethanol. The ethanol was then removed under vacuum. The residue was dissolved in 30 ml of dichloromethane and was extracted with 50 ml and 2×15 ml of 2N hydrochloric acid. The operation continued with the acid aqueous phase that was basified with 40 ml of aqueous sodium hydroxide solution to pH 11. The product was extracted with 4×35 ml of ethyl acetate. The pooled organic phases were dried with sodium sulfate, filtered and evaporated to dryness under vacuum to give a pale yellow oil weighing 14.7 g, corresponding to ethyl α-(p-methoxyphenyl)-β-(dimethylamino)propionate (Yield: 74%).

Workup

  1. customthe mixture was first purged with nitrogen
  2. filtrationwas then filtered through Celite® 535
  3. washwas washed with 2×165 ml of ethanol
  4. customThe ethanol was then removed under vacuum
  5. dissolutionThe residue was dissolved in 30 ml of dichloromethane
  6. extractionwas extracted with 50 ml and 2×15 ml of 2N hydrochloric acid
  7. extractionThe product was extracted with 4×35 ml of ethyl acetate
  8. dry with materialThe pooled organic phases were dried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness under vacuum
  11. customto give a pale yellow oil

Sources & evidence

ORD record
ord-bf6d4213c8c242e1a4a4bea1e23cddd8
Source dataset
uspto-grants-2003_01
Patent number
US06506941B1

Reaction notes

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