Ethyl Acetate → (E)-N-(3-Chloro-2-propenyl)-N-propyl-3-hydroxybenzylamine

Temperature

50 °C

To a solution of 3.30 g (20 mmoi) of N-propyl-3hydroxybenzylamine in 20 ml of dimethyl sulfoxide were added 1.82 g (20 mmoi) of 1,3-dichloropropene (E/Z =2/1) and 1.38 g (10 mmol) of ground potassium carbonate under ice cooling. The mixture was stirred for 1.5 hours at room temperature and for 3 hours at 50° C., poured into 70 ml of ethyl acetate, washed with 50 ml ×2 of water and 50 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate =9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 2.29 g (yield: 48%) of the above identified compound as an oil.

1. washwashed with 50 ml ×2 of water and 50 ml of saturated sodium chloride aqueous solution
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. concentrationconcentrated under reduced pressure
5. customto obtain 2.29 g (yield: 48%) of the

ORD record

ord-a1f539f1ca9546c9994b0f2f8a214ab6

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05436354