Methyl Ethyl Ketone → HCID 86749780, compound

HRID 741547Notes

Reaction equation

HRID 741547 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]=[CH2:5].Br[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21](=O)CC>>[CH2:20]([CH:7]([CH2:8][C:9]([OH:11])=[O:10])[N:2]([CH3:1])[CH2:3][CH:4]=[CH2:5])[CH3:21]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 69391N-Methylallylamine

Product 1

HCID 86749780HCID 86749780, compoundYield 63%

Conditions

Temperature
50 °C

Procedure

A mixture of N-methyl-2-propen-1-amine (2.7 ml), ethyl 3-bromo-propanoate (4.5 ml) and potassium carbonate (5.8 g) in 2-butanone (20 ml) was stirred at 50° C. for 4 hours. The mixture was cooled to room temperature, filtered and the filtrate evaporated. The residue was dissolved in water, extracted with CH2Cl2 and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 9.75/0.25). The pure fractions were collected and evaporated, yielding 3 g (63%) of ethyl N-methyl-N-2-propenyl-β-alanine (interm. 3).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with CH2Cl2
  6. customthe solvent evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 9.75/0.25)
  8. customThe pure fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-72cee4ee36c7418e88ec0e69b0779e36
Source dataset
uspto-grants-1996_09
Patent number
US05552399

Reaction notes

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