Acetic Acid → 1-Cyclopropyl-4-(4-nitrophenyl)piperidine

Participants

Reaction Steps

4-(4-Nitrophenyl)piperidine (1.00 g, 4.85 mmol) was dissolved in 80 mL MeOH and 2 mL HOAc. To it was added (1-ethoxycycloproxy)trimethylsilane, and the mixture was stirred at RT for 40 min To it was then added NaBH3CN (1.83 g, 29.0 mmol), and the mixture was stirred in 65° C. bath for overnight. It was concentrated in vacuo to dryness, diluted with 120 mL EtOAc, washed with 1N NaOH and water ×2, dried, concentrated in vacuo, and subjected to silica flash column using 0 to 4% MeOh in DCM to isolate 1-cyclopropyl-4-(4-nitrophenyl)piperidine (256). It was dissolved in 50 mL EtOAc. To it was added 10% Pd/C (0.5 g), and the mixture was hydrogenated using a H2 balloon at RT for overnight. The mixture was filtered through celite, and concentrated in vacuo to give 4-(1-cyclopropylpiperidin-4-yl)aniline (257) (960 mg, 91% overall) as a white solid.

Provenance & Evidence