Sodium Carbonate → HCID 10707808, compound

Participants

Reaction Conditions

Reaction Steps

1-Benzyl-4-(2-methoxyphenyl)piperidin-4-ol (4.5 g, 15.15 mmol) was mixed with anhydrous potassium bisulphate (8.0 g, 58.56 mmol) and heated to 160° C. under vacuum at 10 mm Hg for 0.5 h. The flask was cooled, the contents dissolved in water and the solution was saturated with sodium carbonate and extracted with ether (2×1100 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure and the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:1) to furnish 1-benzyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2.0 g, 45%). 1H NMR (200 MHz, CDCl3): δ 2.551-2.573 (m, 2H), 2.67-2.71 (m, 2H), 3.16-3.19 (brs, 2H), 3.66 (s, 2H), 3.79 (s, 3H), 5.76-5.78 (brs, 1H), 6.83-6.92 (m, 2H), 7.15-7.41 (m, 7H); m/e=279 (M+).

Provenance & Evidence