4-Isopropylaniline → 4-Isopropyl-N-(2,2-diethoxyethyl)aniline

HRID 610049

Reaction equation

HRID 610049 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].C(=O)(O)[O-].[Na+]>C(O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 74644-IsopropylanilineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

Product 1

HCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)anilineYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-isopropylaniline (7.6 mL, 56 mmol), 2-bromoacetaldehyde diethyl acetal (5.5 mL, 36 mmol) and sodium bicarbonate (4.8 g, 57 mmol) in ethanol (60 mL) was stirred at reflux for 3 days under argon. After cooling to room temperature, the ethanol was removed in vacuo and the product was partitioned between ether and water, washed sequentially with water and brine, and dried over sodium sulfate. After removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes) yielded 4-isopropyl-N-(2,2-diethoxyethyl) aniline (8.23 g, 90%).

Workup

  1. temperatureat reflux for 3 days under argon
  2. customthe ethanol was removed in vacuo
  3. customthe product was partitioned between ether and water
  4. washwashed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4bc69996890742b593cb12a4b60e9adc
Source dataset
uspto-grants-1999_12
Patent number
US05998462

Linked notes

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