4-Iodoaniline → HCID 66790184, compound

Participants

Reaction Steps

4-methyl-Boc-piperidinone (intermediate I.1.a.1, 863 mg, 4.05 mmol) was dissolved in glacial AcOH (4.05 mL). To the resulting solution was added 4-iodo-aniline (0.886 g, 4.05 mmol) and trimethylsilylcyanide (0.647 mL, 4.86 mmol). The reaction mixture was stirred at rt for 1 h, cooled to 0° C., poured onto 7 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 3:1 cis:trans isomeric mixture. LRMS (M+1-CN)=416.

Provenance & Evidence