Chloride → 7-Phenylazepan-2-one

Participants

Reaction Conditions

Reaction Steps

To a 250 ml round-bottomed flask equipped with N2 inlet were added 7.33 g (38.8 mmol) 2-phenylcyclohexanone oxime (Chem. Ber., 55, 3664 (1922)) and 25 ml pyridine. The solution was cooled to 0° C. and 9.61 g (50.4 mmol) p-toluenesulfonyl chloride was added. The reaction was allowed to stir overnight as the ice melted, and then poured into water. Excess chloride was skimmed off the surface, and the reaction mixture was stirred at pH 4 for 3 hours. The precipitate was filtered, washed with water, and dried to a solid, 4.65 g (55%), mp 135°-137° C. (J. Am. Chem. Soc., 82, 4671 (1960)gives mp 139°-141° C.).

Provenance & Evidence