Water → HCID 14986825, compound

Participants

Reaction Steps

A solution of 1-(4-azatricyclo[4.3.1.1(3,8)]undec-4-yl)-3-bromo-1-propanone (1.96 g, 6.8 mmol), 1-(3-chlorophenyl)piperazine hydrochloride (1.60 g, 6.8 mmol) and diisopropylethylamine (2.4 mL, 14 mmol) in anhydrous dimethylformamide (100 mL) was heated at 60° C. for 19 hours. The reaction mixture was poured into water (700 mL) and extracted with ethyl acetate (2×200 mL). The combined organic layers were dried, preadsorbed onto silica gel, and purified by flash chromatography (8 cm diameter, gradient elution with 2-5% methanol in dichloromethane). The resulting solid was recrystallized from ethyl acetate in hexane to yield a light tan solid (1.4 g, 51%, m.p. 110°-112° C.).

Provenance & Evidence