Potassium Carbonate → 1-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidine

Participants

Reaction Steps

A mixture of 4-methoxycarbonyl-4-phenylpiperidine (8.5 g, 0.039 mol), 3-bromopropylamine hydrobromide (12.7 g, 0.058 mol), potassium carbonate (13.475 g, 0.0957 mole), and KI (3.24 g, 0.0195 mol) in 1,4-dioxane (200 mL) was stirred and refluxed for 24 hours. Dioxane was evaporated at reduced pressure, the residue was treated with ice-cold 6 N NaOH (400 mL) and extracted with CH2Cl2 (4×120 mL). Solvent was evaporated from the combined dried (K2CO3) extracts and the residue was purified by column chromatography on silica gel using CHCl3/MeOH/ 2 M NH3 in MeOH (20:2:1) as the eluent to afford the product as a viscous oil (7.8 g, 72%).

Provenance & Evidence