Acetone → 1-[2-(2-Tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine

Participants

Reaction Steps

To 2-tert-butyl-5-nitrophenol (1.01 g) and K2CO3 (1.72 g) was added acetone (35 mL) and H2O (10.5 mL), then 1-(2-chloroethyl)piperidine HCl (1.909 g) and TBAI (153 mg). The mixture was stirred at reflux overnight. Additional K2CO3 (850 mg) and 1-(2-chloroethyl)-piperidine HCl (950 mg) were added and the mixture was heated at reflux for 6 h. The mixture was concentrated in vacuo to an aqueous layer which was acidified with 2 N HCl and extracted with EtOAc. The aqueous layer was basified with 6 N NaOH and washed with CH2Cl2 (3×). The combined organic layers were washed with brine/1 N NaOH and dried over Na2SO4. Washed the EtOAc layer with 2 N NaOH/brine and dried over Na2SO4. The crude material was purified by silica gel column chromatography with 15% EtOAc/Hexanes to yield 1-[2-(2-tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine as a light tan solid.

Provenance & Evidence