Acetonitrile → 4-((1S,4S)-5-Isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine

Participants

Reaction Steps

4-Fluoronitrophenyl (4.00 g, 28.348 mmol), DiPEA (5.89 mL, 60.667 mmol, 2.14 equiv.) and (1S,4S)-2-BOC-2,5-diazabicyclo[2.2.1]heptane (6.02 g, 30.333 mmol, 1.07 equiv.) are mixed in acetonitrile (20 mL). The resulting solution is heated to reflux overnight, after which full conversion has occurred. The solvent is removed under vacuum, and the solid yellow residue is stirred in cyclohexane (50 mL) for 0.25 h, then allowed to settle, the supernatant is discarded, and the process is repeated twice. On the third time, the solid is separated by filtration, allowed to dry under suction, to afford the title compound clean as a yellow solid (8.8 g).

Provenance & Evidence