Diisopropylethylamine → (4-Hydroxy-4-phenyl-piperidin-1-yl)-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]-methanone

Participants

Reaction Steps

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.04 g, 0.2 mmol) and 4-phenyl-piperidin-4-ol (0.041 g, 0.23 mmol) were dissolved in acetonitrile (3 mL). HATU (0.24 mmol) and diisopropylethylamine (0.077 mL, 0.45 mmol) were added and the reaction mixture was stirred. After 1 hour the solvent was evaporated under vacuum and the residue stirred with aqueous sodium hydroxide (1 N, 3 mL) for 0.5 hours. The mixture was diluted with ethyl acetate and washed with brine, dried over magnesium sulphate, filtered and the solvent evaporated under vacuum. The residue was purified by flash chromatography on silica eluting with ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.041 g) as a white solid.

Provenance & Evidence