Isopropyltriphenylphosphonium iodide → 1-Benzyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine

Participants

Reaction Steps

n-Butyl lithium (1.6M, 8.1 ml, 12.93 mmol) is added to a suspension of isopropyltriphenylphosphonium iodide (5.6 g, 12.93 mmol) in dry THF. The ylide is allowed to generate for 45 min at 20°-25° under nitrogen before a solution of 1-benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine (XXI, EXAMPLE 13, 2.0 g, 6.5 mmol) in dry THF is added. The reaction is stirred an additional 30 min before being quenched with water and extracted with chloroform. The extracts are washed with saline and dried (sodium sulfate). Removal of the solvent gives a residue which is chromatographed (silica gel, 4×35 cm column; ethyl acetate/hexane (1/3→1/1) to give the title compound, NMR (300 MHz, CDCl3) 1.55-1.65, 1.74, 1.79-1.85, 1.85, 2.75, 2.87-2.90, 3.40-3.48, 3.42, 5.97, 6.69, 7.16-7.28 and 8.04δ.

Provenance & Evidence