Reaction #82143

Reaction equation

N-Allylphenylamine

bromopentane

sodium hydroxide

→

N-allyl-N-pentylphenylamine

Yield 56.2%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ether (80 ml)
2. 2
   DryingThe extract was dried over potassium carbonate, filterd
3. 3
   Concentrationconcentrated in vacuum
4. 4
   OtherThe residue was chromatographed on silica gel

Procedure

N-Allylphenylamine (1.95 g, 14.7 mmol) and bromopentane (2.22 g, 14.7 mmol) were stirred at 80° C. for 16 hours. After cooled to room temperature, the mixture was treated with a solution of sodium hydroxide(714 mg, 17.9 mmol) in water (1.5 ml), stirred for 30 minutes and extracted with ether (80 ml). The extract was dried over potassium carbonate, filterd and concentrated in vacuum. The residue was chromatographed on silica gel to give N-allyl-N-pentylphenylamine (1.68 g) in 56% yield as a colorless oil.

Source