Toluene → Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Benzyl 4-hydroxypiperidine-1-carboxylate (5 g, 21.25 mmol), tetrabutylammonium hydrogensulfate (0.361 g, 1.06 mmol) and 2-chloro-N,N-dimethylacetamide (4.13 g, 27.63 mmol) were added to toluene (50 mL) to this was added sodium hydroxide (21 g, 210.02 mmol) in water (30 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired compound as an orange liquid (6.00 g, 88% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.65-1.55 (2H, m), 1.93-1.86 (2H, m), 2.95 (3H, s), 3.03 (3H, s), 3.25-3.18 (2H, m), 3.63-3.57 (1H, m), 3.85-3.79 (2H, m), 4.17 (2H, s), 5.12 (2H, s), 7.38-7.30 (5H, m).

Provenance & Evidence