Diisopropylethylamine → (4,4-Difluoro-piperidin-1-yl)-[6-(1-isopropyl-piperidin-4-yloxy)-benzo[b]thiophen-2-yl]-methanone

Participants

Reaction Steps

In a flask were mixed together the above prepared 6-(1-isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid (0.147 g, 0.320 mmol, corrected for purity), 4,4-difluoropiperidine hydrochloride (0.060 g, 1.2 eq.), (benzotriazol-1-yloxy)-tris-(dimethylamino)phosphonium hexafluorophosphate (0.170 g, 1.2 eq.) and 2.5 eq. of N-ethyldiisopropylamine (0.760 mL) in 2 mL of abs. THF and allowed to react during one night at ambient temperature. Pouring onto crashed ice/AcOEt/NH4Cl-solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, CH2Cl2/MeOH=9/1) produced 0.103 g of the title compound as white foam.

Provenance & Evidence