1-[(6-Chloropyridin-3-yl)methyl]-4-methylpiperazine → 5-((4-Methylpiperazin-1-yl)methyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a sealed tube under nitrogen was added 1-((6-chloropyridin-3-ylmethyl)-4-methylpiperazine (13.5 g, 59.8 mmol, Eq:1.00), 2-(dicyclohexylphosphino)biphenyl (4.19 g, 12.0 mmol, Eq:0.20), tris(dibenzylideneacetone)-dipalladium (0) (5.48 g, 5.98 mmol, Eq: 0.10), and lithium bis(trimethylsilyl)amide, 150 ml of a 1.0M solution in THF. An additional 150 ml THF was added. The flask was degassed with argon. The flask was capped and the reaction heated at 100° C. overnight. 3M HCl was added along with DCM to the material and the layers were separated. The aqueous layer was bacidified with 3M NaOH. The aqueous layer was then extracted 3 times with DCM to provide 3.2 g (25.9%) of a yellow powder which was used without further purification.

Provenance & Evidence