p-Fluoronitrobenzene → HCID 66670026, compound

Participants

Reaction Steps

A mixture of 4-fluoro-nitrobenzene (10 g, 71.0 mmol), 4-hydroxy-1-methyl-piperidine (16.6 ml, 141.8 mmol, 2 eq.), tetrabutylammonium bromide (4.6 g, 14.2 mmol, 0.2 eq.), toluene (50 ml) and a 25% aqueous solution of potassium hydroxide (50 ml) is stirred for 15 h at 60° C. The reaction mixture is cooled to RT and poured onto ice/water. The resulting suspension is filtered and the filtrate is extracted with EE. The organic phase is washed with 0.5 N HCl, brine, then dried (sodium sulfate), filtered, and concentrated to afford 6 g of the title compound. The aqueous layer is made neutral by addition of sodium bicarbonate and extracted with EE. The organic phase is washed with brine, dried (sodium sulfate), filtered, and concentrated to afford additional 10 g of the title compound: ESI-MS: 237.0 [MH]+; tR=2.61 min (purity: 90%, gradient J).

Provenance & Evidence