Vinyl chloroformate → 6-Methoxy-8-(4-piperidin-4-ylpiperazin-1-yl)quinoline

Participants

Reaction Steps

A solution of 8-[4-(1-benzylpiperidin-4-yl)piperazin-1-yl]-6-methoxyquinoline (Step 1, 0.22 g) and vinylchloroformate (0.067 mL) in anhydrous CH2Cl2 (5 mL) was stirred at reflux for 1 hour. The reaction was cooled to room temperature and then concentrated on a rotary evaporator. The residue was taken up in dioxane (5 mL), treated with concentrated HCl (0.35 mL) and stirred at room temperature for 1 hour. The resulting reaction was concentrated on a rotary evaporator, taken up in ethanol (1 mL) and stirred at 50° C. for 30 minutes. The reaction was again concentrated on a rotary evaporator and partitioned between CH2Cl2 and 1N aqueous NaOH. The organic layer was washed with water and then brine and was then dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using ethyl acetate/methanol/conc, NH4OH to give 0.14 g of the desired product as a yellow oil; MS (ES) m/z (relative intensity); 326 (M+H)+ (100).

Provenance & Evidence