3-Pyridinemethanamine → HCID 178479881, compound

Participants

Reaction Steps

A solution of 329 mg (1.2 mmol) of 8-chloro-5-methyl-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione (Hunziker F., et al., Helv. Chim. Acta, 50:1588 (1967)) in 10 mL of 2-ethoxyethanol was treated with 0.3 mL (2.4 mmol) of 3-(aminomethyl)pyridine and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed three 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 as an oil. Chromatography on silica gel, eluting with CHCl3 /MeOH (98/2) gave 160 mg (38.4% yield) of the product as a golden solid foam. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =349.

Provenance & Evidence