(4-Bromobutoxy)benzene → 1-(4-Phenoxybutyl)piperazine

Participants

Reaction Steps

A mixture of 45.8 g (0.2 moles) of 4-phenoxybutyl bromide and 45.6 g (0.4 moles) of 1-formylpiperazine in 500 ml of 2-propanol was heated at reflux for 18 hours. The mixture was cooled and filtered. The filter was washed with 2-propanol and the filtrate was evaporated to a paste in vacuo. Water was added and the mixture was extracted three times with 200 ml portions of chloroform. The extracts were combined and evaporated to dryness. Then 250 ml of 5N sodium hydroxide was added to the residue. The mixture was refluxed for 18 hours with stirring, cooled and extracted twice with 250 ml portions of chloroform. The extracts were combined, dried over magnisium sulfate and evaporated to an oil. The oil was distilled bp 153°-156° C./0.05 mm of mercury and gave 33.4 g of 1-(4-phenoxybutyl)piperazine as a colorless liquid which crystallized on standing, mp 35°-36° C.

Provenance & Evidence