1H-Imidazole-1-propanamine → HCID 178477863, compound

Participants

Reaction Steps

A solution of 0.6 g (2.3 mmol) of 8-chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 15 mL of 2-ethoxyethanol was treated with 0.6 mL (4.6 mmol) of 1-(3-aminopropyl)imidazole and heated at reflux for 3 days. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed four times with H2O, then saturated NaHCO3 solution, and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Trituration with EtOAc/hexane followed by recrystallization from acetone/water gave 506 mg (62.6% yield) of the pure product as a golden solid, mp 228-230° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =352.

Provenance & Evidence