Dimethyl Sulfide → HCID 21459871, compound

Participants

Reaction Conditions

Reaction Steps

trans-3 -Nitro-6-oxo-2-phenylpiperidine (80 g, 0.364 mol) was suspended in methanol:dichloromethane (Example 1a, 1:1, 500 ml) under nitrogen. The suspension was cooled to 0° C. and potassium t-butoxide (44.8 g, 0.4 mol) was added in portions over 30 mins. The cooling bath was then removed and the solution stirred for a further 15 mins to afford a clear yellow solution. The solution was then cooled to -78° C. and ozone bubbled through the reaction mixture for 4.5 hrs, the flow of ozone was then stopped and the mixture purged with a stream of nitrogen. Anhydrous dimethyl sulphide (53 ml, 0.73 mol) was then added dropwise and the reaction mixture allowed to warm to room temperature. The solvent was then removed at reduced pressure and the residual orange solid dissolved in dichloromethane (800 ml), washed with water (2×200 ml), dried (MgSO4), the solvent was then removed at reduced pressure. The residue was suspended in ether, filtered, and the pale yellow crystalline solid washed with ether (3×100ml) and dried under vacuum to afford 2,5-dioxo-6-phenylpiperidine (54 g, 78%): m.p. 160°-164° C.; 1H NMR (360 MHz, DMSO-d6) δ2.55-2.58 (2H, m, CH2), 2.63-2.70 (2H, m, CH2), 2.5-2.9 (4H, m, CH2CH2), 4.96 (1H, d, J=2.4 Hz, PhCH), 7.4-7.7 (5H, m, Ar), 8.2 (1H, brs, NH); m/z (CI+) 207 (M+NH4 +), 190 (M+H); Calculated for C11H11NO2C; 69.83; H, 5.86; N, 7.40%. Found C, 70.04; H, 5.77; N, 7.60%.

Provenance & Evidence