Dimethylformamide → 4-[3-[(3-Methylpiperidin-1-yl)methyl]phenoxy]butanamine

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Reaction Steps

5.13 g (0.025 mol) of 3-((methylpiperidin-1-yl)methyl) phenol (Example 64 a) are added to a suspension of 1.0 g (0.025 mol) of sodium hydride (60%) in absolute DMF and the mixture is stirred overnight at room temperature. After the addition of 2.58 g (0.025 mol) of 4chlorobutyronitrile, the reaction mixture is stirred at 60° C. for 7 hours, and then poured into ice water and extracted with ether, and the organic phase is washed with 5% NaOH. After dehydration over Na2SO4, the ethereal phase is introduced dropwise into a suspension of 1.14 g (0.03 mol) of LiAlH4 in absolute ether and then hydrolysed with 2.2 ml H2O. After removal of the inorganic constituents by filtration and evaporation of the solvent under vacuum, 3.66 g of a pale yellow oil are left behind.

Provenance & Evidence