1-(2-Hydroxyethyl)piperazine → HCID 14373548, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluorobenzonitrile (6.0 g, 50 mmoles) and 1-(2-hydroxyethyl)-piperazine (6.5 g, 50 mmoles) were combined in 500 mL of dimethylformamide and heated at 80° C. under N2 for 24 hours. After cooling, the solvent was removed in vacuum and the crude 1-(2-hydroxyethyl)-4-(2-cyanophenyl)piperazine thus produced was used without purification. 2.3 Grams (10 mmole) of the crude 1-(2-hydroxyethyl)-4-(2-cyanophenyl)piperazine was dissolved in 100 mL of CH2Cl2 and 1.3 g (10 mmole) of diisopropyl ethylamine was added, followed by addition of 2.0 g (10 mmole) of 1-adamantanecarbonyl chloride. The mixture was stirred at room temperature for 3 hours, washed with saturated NaHCO3 solution, saturated brine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was column chromatographed on 100 g of silica gel with CHCl3 and the product thus obtained was crystallized from isopropanol with the addition of 4N isopropanolic HCl to give 1.1 g of title compound as the monohydrochloride salt, mp. 230°-231° C.

Provenance & Evidence