Iodoethane → N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine

HRID 2423226Notes

Reaction equation

HRID 2423226 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([CH3:16])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[CH2:17](I)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][C:5]([CH3:6])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67243335N-ethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine

Product 1

HCID 67242349N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 100 mL round bottom flask was charged N-ethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine (1.50 g, 6.75 mmol), anhydrous acetonitrile (22 mL), ethyl iodide (1.16 mL, 7.43 mmol), and potassium carbonate (1.87 g, 13.5 mmol). The reaction was brought to reflux for 4 h. The reaction mixture was filtered and concentrated in vacuo. The residue was diluted with water and ethyl acetate and layers were separated. The organic layer was washed with once each with water, and then with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine (1.45 g, 86.1%). LC/MS (ESI+) 251 (M+H)+.

Workup

  1. temperatureto reflux for 4 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water and ethyl acetate and layers
  5. customwere separated
  6. washThe organic layer was washed with once each with water
  7. dry with materialwith brine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11e9a67a21ba46a282819d942c62ad56
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

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