Tetrahydrofuran → N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl)-acetamide

Participants

Reaction Steps

To a solution of 1-methyl-4-piperidinemethanol (0.566 g, 4.3 mmol) in THF (25 ml) at 0° C. was added, portion wise, 60% NaH (0.63 g, 15.48 mmol) and the mixture stirred for 15 mins. N-(5-Fluoro-4-methoxy-2-nitro-phenyl)-acetamide [U.S. Pat. No. 4,431,807] (1 g, 4.38 mmol) in THF (40 ml) was added to reaction, which was stirred at RT for 30 mins followed by heating at 50° C. for 1 hour. The reaction was quenched with water and then extracted with EtOAc twice, the organic portion was washed with brine, dried over MgSO4, filtered and reduced in vacuo to yield N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl]-acetamide (1.34 g), (LC/MS (acidic method): Rt 1.84, [M+H]+ 338)

Provenance & Evidence