Water → HCID 10039345, compound

Participants

Reaction Steps

To a solution of cycloheptanone (56.1 g, 0.5 mol) in toluene (500 ml) was added morpholine (65.3 g, 0.75 mol) and tosic acid (100 mg). The reaction vessel was fitted with a Dean-Stark condenser and the reaction was refluxed for 24 hours. The toluene was removed in vacuo and the enamine was vacuum distilled. The enamine was collected as a pale yellow oil (46.5 g, 51%). To a solution of the enamine (10.0 g, 0.055 mol) in dioxane (50 ml) was added 2-bromobenzyl bromide and the reaction was refluxed overnight. Water (10 ml) was then added and the mixture was refluxed an additional 2 hours. The reaction was cooled and the solvent was removed in vacuo. The residue was partitioned between dichloromethane and 1N hydrochloric acid. The dichloromethane layer was washed with additional 1N hydrochloric acid (50 ml) and water (50 ml), dried (MgSO4), filtered, and reduced in volume to yield a crude orange oil (15.9 g). The mixture was vacuum distilled to yield the title compound as a clear oil (8.5 g, 55%) that was a semisolid at 23° C.

Provenance & Evidence