1-Methyl-4-(piperidin-4-yl)piperazine → HCID 71239606, compound

Participants

Reaction Steps

A suspension of [(4-bromophenyl)ethynyl](trimethyl)silane (2.210 g, 8.73 mmol), Pd2(dba)3 (0.400 g, 0.436 mmol), 2-dicyclohexylphosphino-2′-(N,N′-dimethylamino)biphenyl (0.172 g, 0.436 mmol) in anhydrous THF (60 mL) was degassed and backfilled with Argon for three times. 1-Methyl-4-(piperidin-4-yl)piperazine (4.00 g, 21.82 mmol) was added and the mixture was degassed and backfilled with Argon for three times again. Finally LiHMDS 1 M in THF (17.46 mL) was added by a syringe and the mixture was heated to reflux for 2 h. After cooling to room temperature the reaction mixture was filtered on a pad of celite washing with THF (300 mL). The filtrate was evaporated under vacuum and the black oil so obtained was purified by flash chromatography on silica gel (DCM/MeOH/NH4OH 90/10/0.2) to afford the title compound as a yellow solid (2.55 g, 82%).

Provenance & Evidence