Triethylamine → (4-Phenoxyphenyl) 4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

A solution of the carbonate(45 g, 0.13 mol) produced in Example 1 in 250 mL of methylene chloride was added dropwise under nitrogen over three hours to a solution of 4-hydroxypiperidine (14.3 g, 0.14 mol) and triethylamine (19.7 mL, 0.14 mol) in 250 mL of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for 4 hours and 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 39.27 g of a light yellow solid. Recrystallization from diisopropyl ether-methanol gave 31.78 g (79%) of the title compound as an off-white crystalline solid, mp 130-133° C.

Provenance & Evidence