Water → [2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

Beteiligte Stoffe

Reaktionsschritte

Lithium aluminium hydride (0.11 g, 2.9 mmol) was slurried in ether (15 mL) under nitrogen with stirring. A solution of 2-(4-fluorophenyl)-N-methylpent-4-enamide (0.20 g in 5 mL of ether, 0.97 mmol) was added carefully and the mixture was then stirred at room temperature overnight. Water (0.11 mL) was added dropwise followed by a solution of NaOH (0.11 mL of a 15% aqueous solution) and then water (0.33 mL) again. The mixture was stirred for 10 min and then filtered. The filter cake was washed with ether and the combined solutions were washed several times with water. The organic solution was dried over MgSO4 and the solvent was removed by evaporation. There was obtained 0.16 g (86%) of [2-(4-fluorophenyl)pent-4-en-1-yl]methylamine as an oil. 1H NMR (400 MHz, CDCl3): 2.4-2.6 (m, 5H), 2.7-2.9 (m, 3H), 4.9-5.0 (m, 2H), 5.6-5.8 (m, 1H), 7.0 (m, 2H), 7.1 (m, 2H); LCMS: m/z 194 (M+1)+.

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