Methyl iodide → 1'-cycloheptyl-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one

Participants

Reaction Steps

1′-cycloheptylspiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one hydrochloride (compound No. 5) (188 mg, 0.54 mmol) was suspended in anhydrous dimethylformamide (4.0 mL), treated with sodium hydride (48 mg, 60% dispersion in mineral oil, 1.2 mmol) and stirred at room temperature for 10 minutes under nitrogen. The reaction mixture was then treated with a solution of methyl iodide (92 mg, 0.65 mmol) in anhydrous dimethylformamide (1.0 mL) and stirred at room temperature for 1 hour. The reaction mixture was diluted with water (50 mL), and the product was extracted in dichloromethane (2×50 mL). The pooled extracts were washed with water (2×10 mL), saturated NaHCO3, (2×10 mL) and saturated brine (2×10 mL); then dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford crude 1′-cycloheptyl-1-methylspiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one (compound no. 65) free base as a colorless oil.

Provenance & Evidence