HCID 10617412, compound → HCID 10519343, compound

Participants

Reaction Steps

1-Benzyl-4-[N-methyl-N-(3-nitro-6-fluoro-2-pyridinyl)amino]piperidine (EXAMPLE 151, 5.81 g, 16.87 mmol) and platinum oxide (2.5 g) in ethanol (150 ml) is hydrogenated at 10 p.s.i. of hydrogen for one hr. Filtration and removal of the solvent gives 1-benzyl-4-[N-methyl-N-(3-amino-6-fluoro-2-pyridinyl)amino]piperidine. Without further purification, this material is dissolved in 85 ml acetonitrile and cooled to 0°. Acetone (3.76 ml, 51.2 mmol) and fused zinc chloride (465 mg, 3.4 mmol) are added and the mixture refluxed for 8 hrs. It is then poured into water and extracted with chloroform. The extract is dried over sodium sulfate, filtered and concentrated. Chromatography of the concentrate (silica gel, 300 g; ethyl acetate/hexane (50/50)) gives the title compound, NMR (300 MHz, CD3OD) 7.64, 7.36-7.41, 6.73, 3.60, 3.35, 3.00, 2.74, 2.10-2.20, 1.81 and 1.77δ.

Provenance & Evidence