18-Crown-6 → HCID 22914705, compound

Participants

Reaction Steps

1-(N-chloro-4-piperidyl)-3,1-benzoxazin-2-one from Step 1 above (230 mg, 0.86 mmol) was dissolved in warm ether (30 mL) and the solution was added dropwise to a suspension of potassium superoxide (135 mg, 1.9 mmol) and 18-crown-6 (10 mg, 0.04 mmol) in ether (10 mL). The mixture was stirred at ambient temperature for five days, with two additional lots of 135 mg each of potassium superoxide being added on the second and third days. The reaction was filtered and the filtrate was added dropwise to an ether solution of trimethylsilylcyanide (0.172 mL, 128 mg, 1.3 mmol). The mixture was stirred at ambient temperature for 18 hours, then evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 4:96 MeOH:CH2Cl2. The combined product fractions were evaporated to dryness in vacuo, and the residue was evaporated twice from ether to give 1-(2-cyano-4-piperidyl)-3,1-benzoxazin-2-one: MS (FAB): M+H @ m/e=258.

Provenance & Evidence