Triethylamine → HCID 18695630, compound

Participants

Reaction Conditions

Reaction Steps

3.2 g (14.3 mmol) of 3-cyclopentyloxy-4-methoxy-phenylamine (Garcia et al., JOC, 2005, 70, p 1050) were dissolved in 120 ml of DCM. The solution was cooled to 0° C. and 15 ml (107.6 mmol, 7.5 eq.) triethylamine and 3.7 g (26.1 mmol; 1.8 eq) nicotinoyl chloride in 50 ml DCM were added to the reaction mixture. The reaction mixture was stirred for 2 h and then a solution of 1.3 g NaOH in 50 ml water was added to the mixture. The organic phase was separated and washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (ethyl acetate/n-hexane 1:1) to afford 4 g (85%) of the desired product as a white solid.

Provenance & Evidence