alpha-Chloro-m-nitrotoluene → 1-Methyl-4-[(3-nitrophenyl)methoxy]piperidine

Participants

Reaction Steps

4-Hydroxy-1-methylpiperidine (11.5 g, 0.1 mol) is dissolved in 250 mL dichloromethane. A solution of 100 g NaOH in 100 mL of water is added followed by 17.2 g (0.1 mol) 3-nitro-benzylchloride and a catalytic amount of benzyl-triethylammonium chloride. The mixture is stirred very efficiently during 2 h at rt and then poured into 300 mL of ice-cold water. The organic layer is separated and the organic phase extracted once more with dichloromethane. The organic phase is extracted with 1N HCl (2×200 mL) and the aqueous extracts adjusted to pH 9-10 by the addition of solid sodium carbonate. The basic solution is extracted with ethyl acetate (2×200 mL) and the organic phase washed with brine, dried over potassium carbonate and evaporated. 1-Methyl-4-(3-nitro-benzyloxy)-piperidine is obtained as brown viscous oil. HPLC: 1.35 (System XS); [M+H]+ 251.0.

Provenance & Evidence