Acetyl chloride → HCID 22141181, compound

Participants

Reaction Steps

To a solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 1.30 g, 4.8 mmol) and triethylamine (3.34 ml, 24.0 mmol) in dichloromethane (30 ml) at room temperature was slowly added acetyl chloride (0.48 ml, 6.72 mmol). The mixture was stirred at room temperature overnight and then saturated ammonium chloride solution (50 ml) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (3×20 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:methanol:ammonia solution (0.880) (90:10:1) to afford the title compound (1.5 g, 100%) as a colourless gum.

Provenance & Evidence