Toluene → 6-Benzyl-1-oxa-6-azaspiro(2,5)octane

Participants

Reaction Conditions

Reaction Steps

18.9 g (0.1 mol) of 1-benzyl-4-piperidone, 24.2 g (0.11 mol) of trimethylsulfoxide iodide salt, 0.5 g of tetrabutyl ammonium bromide and 200 mL of toluene were added to a 500 mL round bottom flask, and slowly added dropwise at room temperature with 60 mL of (15%) sodium hydroxide solution. Then the reaction was heated to 80° C., reacted for 8 h, and then cooled to room temperature. The toluene layer was separated, and the water layer was extracted with toluene (50 mL×3). The toluene layer was combined, washed with water, saturated sodium chloride solution in sequence, dried with anhydrous sodium sulfate, and distilled under reduced pressure to recovery solvent to obtain light yellow oily liquid N-benzyl-1-oxa-6-azaspiro[2,5]-octane 19 g, yield: 93%. 1H-NMR (CDCl3, ppm) δ: 7.31-7.33 (5H, m), 3.56 (2H, s), 2.64 (2H, s), 2.53-2.62 (4H, m), 1.52-1.86 (4H, m).

Provenance & Evidence