Dimethylformamide → 6-Phenylazepan-2-one

Participants

Reaction Steps

27.6 ml of diphenylphosphoryl azide and then 37.5 ml of N-methylmorpholine were added to 260 ml of dimethylformamide containing 26.0 g of 6-amino-5-phenylhexanoic acid hydrochloride [prepared as described in step (c) above] in an ice-bath. The reaction mixture was stirred for 3.5 hours at room temperature, and then dissolved in 0.5 liter of ethyl acetate and 0.5 liter of water. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of ethyl acetate and methylene chloride as eluent, to give 4.0 g of the title compound as crystals, melting at 153.5°-154.5° C. (with decomposition).

Provenance & Evidence