Chloroacetic Acid → (+/-)-cis-Decahydroquinoxalin-2-one

Participants

Reaction Steps

cis-1,2-Diaminocyclohexane (4.1 g, 36 mmol) is dissolved in 150 ml of H2O. Chloroacetic acid (3.4 g, 36 mmol) in 50 ml of H2O is added dropwise at 10° C. in 5 minutes, then potassium carbonate (7.9 g, 57 mmol) in 30 ml of H2O is added dropwise at 10 C. The reaction mixture is allowed to warm slowly to room temperature and stirred 24 hours. The solution is heated at 90° C. for 2 hours, concentrated. The resulting solid is taken-up in boiling toluene (100 ml), filtered while hot, concentrated to give (+/−)-cis-decahydroquinoxalin-2-one (0.8 g, 14% yield) as a white solid. C8H14N2O, MS (M+H)+: 155

Provenance & Evidence