1-Iodopropane → 1-Propylpiperidin-4-ol

1-Iodopropane (22 ml) was added dropwise during 15 minutes to a stirred suspension of 4-hydroxypiperidine (20 g) in acetone (250 ml) and the resultant mixture was stirred at ambient temperature for 20 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and 2N aqueous sodium hydroxide solution. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give 4-hydroxy-N-propylpiperidine as an oil (19.6 g); NMR Spectrum: (DMSOd6) 0.82 (t, 3H), 1.16 (m, 4H), 1.66 (m, 2H), 1.91 (m, 2H), 2.06 (t, 2H), 2.64 (m, 2H), 3.38 (m, 1H), 4.45 (d, 1H); Mass Spectrum: M+H+ 144.