N-Methylaniline → Ethyl 5-[methyl(phenyl)amino]pentanoate

HRID 570899Notes

Reaction equation

HRID 570899 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:10]([CH2:14][CH2:15][CH3:16])[C:11]([O-:13])=[O:12].N1C(C)=CC=[CH:19][C:18]=1C>C(#N)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:10][C:11]([O:13][CH2:18][CH3:19])=[O:12]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 79372,6-LutidineHCID 22174073HCID 22174073, compound

Product 1

HCID 19438629Ethyl 5-[methyl(phenyl)amino]pentanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.52 ml (48 mmol) of N-Methyl aniline, 8 ml Bromovalerate (50.2 mmol) and 2,6-lutidine (5.82 ml, 50.2 mmol) were taken in 100 ml acetonitrile and the reaction was refluxed for 24 hour under stirring. Acetonitrile was removed under vacuum and residues were dissolved in ether. The organic phase was washed with water. After drying over magnesium sulfate and filtering, the solvent was removed to give a brown liquid. The residue was purified by flash chromatography on silica gel using a 10% ethyl acetate in hexane as eluent gave 10.1 g light yellow oil as product. MW C14H21NO2 235.32 g/mol (yields 90%).

Workup

  1. temperaturethe reaction was refluxed for 24 hour
  2. customAcetonitrile was removed under vacuum and residues
  3. dissolutionwere dissolved in ether
  4. washThe organic phase was washed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationfiltering
  7. customthe solvent was removed
  8. customto give a brown liquid
  9. customThe residue was purified by flash chromatography on silica gel using a 10% ethyl acetate in hexane as eluent
  10. customgave 10.1 g light yellow oil as product
  11. customMW C14H21NO2 235.32 g/mol (yields 90%)

Sources & evidence

ORD record
ord-ea4d2a6f980a4bda988e8e7480c2e5de
Source dataset
uspto-grants-2015_05
Patent number
US09023998B2

Reaction notes

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