Sulfuric Acid → 4-Benzyl-2-(chloromethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

41.25 g of 2-[2-(4-chloro-2,3-dihydroindol-1-yl)-2-oxoethyl-2-(2-benzylaminoethoxy)-3-chloropropan-1-ol previously obtained are placed in a 250 ml round-bottomed flask equipped with a condenser, and then 50 ml of concentrated sulfuric acid (d=1.84) are added dropwise. The temperature increases, and the water formed condenses in the condenser. The reaction medium is then heated for one hour at 150° C., then cooled to ambient temperature (20° C.), before being poured slowly onto ice; the reaction medium is brought to pH=10 with 40% NaOH, and then extracted with toluene (2×150 ml), and the organic phases are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. 4-Benzyl-2-chloromethylmorpholine is isolated (20.30 g, light brown oil, yield=54%) and is used in the next step.

Provenance & Evidence