Triethylamine → 4-[[[(6-Hydroxyhexyl)amino]-carbonyl]oxy]-1-piperidinecarboxylic acid 4-phenoxyphenyl ester

Participants

Reaction Steps

A solution of triethylamine (65.5 mL, 0.47 mol) and 6-aminohexanol (13.2 g, 0.11 mol) in 300 mL of methylene chloride was added dropwise under nitrogen to a solution of the carbonate (45.0 g, 0.09 mol) produced in Example 3 in 500 mL of methylene chloride at room temperature. After the addition the solution was stirred at room temperature overnight. The reaction was extracted one time with 1N HCl and then multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 47.0 g of an off-white solid. Recrystallization from methylene chloride-diisopropyl ether gave 35.5 g (83%) of the title compound as a white crystalline solid, mp 69-72° C.

Provenance & Evidence