Aluminium lithium hydride → (E)-4-[(3-phenyl-2-propenyloxy)ethyl]piperidine

Participants

Reaction Steps

Lithium aluminum hydride (1.0 M in tetrahydrofuran, 2.1 mL, 2.1 mmol) was added dropwise over 4 minutes to a -78° C. solution of the above amide (0.72 g, 2.1 mmol) in dry THF with stirring under nitrogen. After 3 hours, the reaction was allowed to slowly warm to room temperature. After 21 hours, Celite® was slurried into the reaction mixture, followed by careful quenching with water (20 mL). The mixture was filtered through a Celite® pad and rinsed with ethyl acetate (100 mL). After phase separation, the organic solution was extracted with water (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel, eluting with ethyl acetate, and concentrated under vacuum to yield (E)-4-[(3-phenyl-2-propenyloxy)ethyl]piperidine (0.18 g, 26%) as a colorless oil. 1H NMR(300 MHz/CDCl3 /TMS, δ): 7.40-7.16(m,10H), 6.60(d,1H,J= 16 Hz), 6.29(dt,1H,J=16,6 Hz), 4.12(dd,2H,J=6,1 Hz), 3.51(t,2H,J=7 Hz), 3.48(s,2H), 2.88-2.85(m,2H), 2.00-1.21 (m,9H). HRMS: Calculated for C23H29NO:335.2249; found: 335.2251.

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