Piperazine → 1-(1-Naphthyl)piperazine

Participants

Reaction Steps

83.2 g (966 mmol) of piperazine, 38.0 g (339 mmol) of potassium tert-butoxide and 50.0 g (241 mmol) of 1-bromonaphthalene were added to a mixture of 5.4 g (24.2 mmol) of palladium acetate and 14.7 g (48.3 mmol) of tri-o-tolylphosphine in 500 ml of xylene and the reaction mixture was heated at reflux for 10 h under a nitrogen atmosphere and while stirring thoroughly. After that, the mixture was diluted with methylene chloride, the insoluble residues were filtered off and the filtrate was evaporated. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 21.5 g (42%) of product having a m.p. of 84-86° C. were isolated.

Provenance & Evidence