Acetic Acid → HCID 59507768, compound

Participants

Reaction Steps

To a solution of 10% acetic acid in methanol was added 4-(2-methoxy-4-nitrophenoxy)piperidine (148 mg, 0.59 mmol, 1 eq), anhydrous acetone (5 eq), and sodium cyanoborohydride (1.5 eq). The solution was stirred at room temperature for 24 h. Reaction is 85% complete. Charged additional anhydrous acetone (5 eq) and sodium cyanoborohydride (1.5 eq) and stirred for 24 h. The solvent was evaporated, the residue brought to pH=10 with sodium carbonate and extracted with EtOAc. The organic layer was washed with water, brine, dried with magnesium sulfate and evaporated to afford 1-isopropyl-4-(2-methoxy-4-nitrophenoxy)piperidine as a yellow oil (163 mg, 97%). LC/MS (m/z): 295.2 (MH+), Rt 1.96 minutes.

Provenance & Evidence