Hydrochloric Acid → HCID 58155259, compound

Participants

Reaction Conditions

Reaction Steps

The (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,6,6-trimethyl-morpholin-3-one (1.13 g; 2.71 mmol) was dissolved in dioxane (80 ml) and the Lawesson's Reagent (691 mg, 1.71 mmol) was added at room temperature. The reaction mixture was stirred at 80° C. for 2 hours. Thereafter, the green solution was cooled to 23° C., then hydrochloric acid (1M, 3.42 ml) was added and the mixture was stirred for 30 minutes at room temperature. For the workup, the reaction mixture was poured into a saturated sodium hydrogen-carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated at reduced pressure to give blue oil (1.33 g). The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 50/50 as the eluent. The (R)-5-(5-amino-2-fluoro-phenyl)-5,6,6-trimethyl-morpholine-3-thione was obtained as a white foam (0.63 g, 86% of theory). Mass (calculated) C13H17FN2OS [268.354]; (found) [M+H]+=269.

Provenance & Evidence