Hydrochloric Acid → HCID 19800164, compound

Participants

Reaction Steps

A solution of 7.2 ml of 2,2,6,6-tetramethylpiperidine in 300 ml of THF was cooled to -5° C. as 25 ml of 1.6M butyllithium (0.04 mol) in hexane was added dropwise. The reaction was stirred 10 min then cooled to -77° C. as 3 ml of 2-chloropyrazine in 7 ml of THF was added dropwise. After another 15 min, 4.4 g of 1-azabicyclo[2.2.1]heptan-3-one (0.0396 mol) in 10 ml of THF was added and the reaction stirred 1 h. A solution of 8 ml of conc. HCl in 4 ml of ethanol was added and the cooling was removed. When the temperature reached -10° C., 100 ml of water was added, the organics were evaporated, and the residue treated with 11 ml of 5N NaOH. The solvent was reduced to a small volume, ca. 50 ml, the mixture cooled in ice-water, and the solid collected by filtration. The aqueous fraction was extracted 3× with 50 ml of CHCl3, the extracts added to the solid filtrate, and the total volume of the mixture taken to 500 ml with more CHCl3. The mixture was heated to boiling, dried, filtered, and the solvent evaporated to give a brown solid. The solid was recrystallized from isopropanol to give 4.1 g of tan crystalline (26), mp 220° C. dec. NMR ppm (CDCl3) 1.55-1.9 (2H, m), 2.27 (1H, m), 2.42-2.58 (2H, m), 2.75 (2H, m), 2.95 (1H, m), 3.5 (1H, d) 3.6 (1H, d), 8.3 (1H, d) 8.42 (1H, d). Anal. C10H12ClN3O requires C: 53.22; H: 5.36; N: 18.62%. Found C: 53.10; H: 5.20; N: 18.41%.

Provenance & Evidence