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

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.

1. waitAfter 21 hours
2. customby careful quenching with water (20 mL)
3. filtrationThe mixture was filtered through a Celite® pad
4. washrinsed with ethyl acetate (100 mL)
5. customAfter phase separation
6. extractionthe organic solution was extracted with water (20 mL), brine (20 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by chromatography on silica gel
11. washeluting with ethyl acetate
12. concentrationconcentrated under vacuum

ORD record

ord-2fd0f5bd9f5e445d9a02cf6f041b4eee

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05317024