Methylamine → trans-4-(3-Chlorophenyl)-but-3-enylamine

Participants

Reaction Steps

A solution of trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (0.50 g) and methylamine (2 M in tetrahydrofuran, 8 mL) in 20 mL ethanol was heated to reflux for 4 h. The solution was cooled to rt and the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate and extracted 3 times with 1 M hydrochloric acid. The combined acid layers were made basic with potassium hydroxide to pH 9 and extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and the solvent was removed in vacuo to yield 0.20 g of trans-4-(3-chlorophenyl)-but-3-enylamine.

Provenance & Evidence