P-Toluenesulfonamide → N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-4-methylphenylsulphonamide

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Reaction Steps

Sodium hydride (300 mg of a 60% suspension) was added to a stirred solution of 4-methylphenylsulphonamide and the mixture stirred at room temperature until effervescence had ceased. N-benzyloxycarbonylpiperidine-4-methanol mesylate (1.09 g) was added and the mixture heated at 100° C. for 7 hours. After cooling to room temperature it was diluted with water (200 ml) and extracted with ether (4×40 ml); the extracts were combined, washed with water (2×) and brine, dried (MgSO4) and evaporated to yield N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-4-methylphenylsulphonamide; NMR (d6DMSO) δ 0.81-1.1(2H,m); 1.5-1.7(3H,m); 2.35(3H,s); 2.6(2H,t); 2.7-2.9(2H,m); 4.0(2H,d); 5.0(2H,s); 7.2-7.5(7H,m); 7.55(1H,t); 7.7(2H,d); m/e 403 (M+H)+.

Provenance & Evidence