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

HRID 2194823Notes

Reaction equation

HRID 2194823 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>CN(C=O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 74644-Isopropylaniline2×HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-isopropylaniline (4.05 g, 30.0 mmol) and potassium carbonate (6.21 g, 45 mmol) in DMF (100 mL) at room temperature was added 2-bromo-1,1-diethoxyethane (6.50 g, 33.0 mmol). The mixture was then stirred at 80-90° C. until all of the 4-isopropylaniline was consumed (24 h). The solvent was removed in vacuo and the residue was treated with dichloromethane (150 mL), washed with water and brine, dried over anhydrous MgSO4, and then concentrated. Chromatography (silica gel, hexanes:ethyl acetate, 9:1) of the crude product, furnished the pure intermediate, N-(4-isopropylphenyl)-2,2-diethoxyethylamine, as a colorless oil (5.71 g, 75.8%). 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.18-1.32 (m, 12H), 2.75-2.91 (m, 1H), 3.24 (d, 2H), 3.52-3.62 (m, 2H), 3.67-3.79 (m, 2H), 3.87 (s, br, 1H), 4.70 (t, 1H), 6.60 (d, 2H), 7.05 (d, 2H).

Workup

  1. customwas consumed (24 h)
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with dichloromethane (150 mL)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c07ea187c68d418580730bfa6ba1db36
Source dataset
uspto-grants-2012_12
Patent number
US08334313B2

Reaction notes

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