4-Bromoanisole → 4-methoxy-N-(oxan-4-ylmethyl)aniline

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (0.090 g, 0.40 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.464 g, 0.80 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-4-methoxybenzene (1 g, 5.35 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.654 mL, 5.35 mmol) and sodium-t- butoxide (0.771 g, 8.02 mmol) were suspended in toluene (7 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. The mixture was diluted with water (250 mL), and extracted with ethyl acetate (200 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and crude fractions were evaporated to dryness to afford 4-methoxy-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (0.270 g, 22.82 %) as a brown oil.

Provenance & Evidence