Hydrochloric Acid → 1-Benzyl-4-(3-phenylpropylidene)piperidine

Participants

Reaction Steps

A solution of 100 mL of 0.5M potassium bis(trimethylsilyl)amide in toluene was added to a mixture of 23.07 g (3-phenylpropyl)triphenylphosphonium bromide from Step A in 150 mL toluene in an ice bath over 15 minute with stirring under nitrogen. After stirring for 15 more minutes, a solution of 8.515 g of 1-benzyl-4-piperidone in 50 mL toluene was added over 30 minutes with stirring. The reaction mixture was stirred as it was allowed to warm to room temperature overnight. After 15 hours, the reaction mixture was poured into 200 mL cold 1N HCl. The layers were separated and the toluene layer was washed with 2×200 mL 1N HCl. The combined HCl solution and an oily interfacial layer was washed with 100 mL toluene. After adding 30 g KOH, the aqueous layer was extraced with 3×150 mL of ether. The combined ether solution was washed with 100 mL each of water and saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography using 10˜15% ethyl acetate in hexanes having 3% (v/v) Et3N to give 8.2 g of the title compound as a colorless oil. RF: 0.38 (10% EtOAc in hexanes having 3% (v/v) Et3N). 1H NMR (500 MHz, CDCl3): δ7.34 (d, 4.3 Hz, 4H), 7.25˜7.30 (m, 2H), 7.17˜7.21 (m, 4H), 5.19 (t, 7.2 Hz, 1H), 3.51 (s, 3H), 2.64˜2.67 (m, 2H), 2.41˜2.44 (m, 2H), 2.29˜2.35 (m, 4H), 2.18˜2.22 (m, 4H).

Provenance & Evidence