1-Benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine → HCID 53895921, compound

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Reaction Steps

To a stirring suspension of (ethyl)triphenylphosphonium bromide (1.75 g, 4.72 mmol) in dry THF (150 ml) at 20°-25° under nitrogen is added n-butyl lithium (1.6M in hexane, 2.95 ml, 4.72 mmol). The resulting mixture is stirred for 10 min followed by addition of 1-benzyl-4-[N-methyl-N-(3-formyl-2-pyridinyl)amino]piperidine (XXI, EXAMPLE 13, 1.40 g, 4.72 mmol) in THF (10 ml) under nitrogen. The mixture is stirred at 20°-25° for 1 hr and quenched with saturated aqueous ammonium chloride (50 ml). Water is added (100 ml) and the aqueous is extracted with ethyl acetate (3×75 ml). The organic phases are combined, dried over sodium sulfate and the solvent evaporated to dryness. The residue is purified via flash column chromatography (silica gel; hexane/ethyl acetate (6/1→1/1)) to give the title compound, NMR (CDCl3) 1.64, 1.81-1.93, 2.80, 2.91, 3.46, 5.77, 6.13, 6.26, 6.40, 6.78, 7.20-7.56 and 8.11δ; MS (EI, m/e) 321 (M+).

Provenance & Evidence