Ethyl Acetate → (E)-3-Chloro-N-methyl-N-(1-naphthylmethyl)-2-propen-1-amine

To a solution of 9.84 g (57.5 mmol) of N-methyl-1-naphthalenemethanamine in 60 ml of dimethyl sulfoxide were added 5.5 ml (60 mmol) of 1,3-dichloropropene (E/Z =9/1) and 8.28 g (60 mmol) of potassium carbonate under ice cooling. The mixture was stirred for 6 hours at room temperature, poured into 250 ml of ethyl acetate, washed with 150 ml ×3 of water and 150 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 10.86 g (yield: 77%) of the above identified compound as an oil.

1. washwashed with 150 ml ×3 of water and 150 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 10.86 g (yield: 77%) of the

ORD record

ord-e224189af5e44bc3bcf368793cebaf2a

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05436354