Triethylamine → HCID 10047715, compound

Participants

Reaction Steps

A solution of isobutyryl chloride (2.34 g, 21.9 mmol) in dry dichloromethane (8 mL) was added over 2 minutes to a solution of N-[4-[4-(6-fluorobenzo[b]thien-3-yl)-1-piperazinyl]butyl]-acetamide (2.51 g, 7.18 mmol), triethylamine (2.18 g, 21.5 mmol), 4-dimethylaminopyridine (0.877 g, 7.18 mmol), and dry dichloromethane (50 mL) at room temperature under a nitrogen atmosphere. After 2.5 hours the reaction solution was diluted with dichloromethane (100 mL), washed with water (75 mL), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with 5% methanol/dichloromethane as eluent to give 2.91 g of an amber solid. Recrystallization from tert-butyl methyl ether/heptane afforded 1.52 g (50%) of the title compound as tan crystals: m.p.=98 °-99° C.

Provenance & Evidence