1-Chloroethyl chloroformate → HCID 11516034, compound

Participants

Reaction Steps

To a solution of 3-bromo-10-(1-methylpiperidin-4-yl)-10H-phenothiazine, 4e (0.6 g, 1.6 mmol) in 1,2-dichloroethane (10 mL) was added 1-chloroethyl chloroformate (276 μL, 2.6 mmol). The mixture was heated to reflux for 1 h, allowed to cool to rt, and evaporated. The residue was dissolved in methanol (10 mL) and heated to reflux for 1 h. Treatment with 1-chloroethyl chloroformate was repeated three more times to obtain ⅔ conversion. After work-up, the residue was purified via flash column chromatography (eluent gradient: 0 to 30% MeOH in EtOAc containing 1% triethylamine) to yield 150 mg of recovered starting material 4e and 382 mg (66%) of title compound 3-bromo-10-piperidin-4-yl-10H-phenothiazine, 5e. MS m/z (MH+) 401.1/403.1.

Provenance & Evidence