4-Iodoaniline → HCID 66791326, compound

Participants

Reaction Steps

Boc-piperidinone (10 g, 50.2 mmol) was dissolved in acetonitrile (50 mL) and concentrated in vacuo twice, dissolved in glacial AcOH (50 mL). To the resulting solution was added 4-iodo-aniline (10.99 g, 50.2 mmol) and trimethylsilylcyanide (8 mL, 60.2 mmol). The reaction mixture was stirred at rt for 1 h, cooled to 0° C., poured onto 50 ml ammonium hydroxide and ice/water, extracted with DCM twice. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the desired product as a purple foam. LRMS (M+1-CN)=401.

Provenance & Evidence