HCID 57447696, compound → HCID 55285919, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phthalimide 300 (5.2 g, 18.9 mmol) and N2H4.H2O (1.9 g, 37.8 mmol) in EtOH (100 mL) was heated at reflux temperature for 3 h. The solution was cooled to 0° C., the solid filtered off and washed with cold EtOH (20 mL) and EtOAc (100 mL). The solvent was evaporated to half volume, stored at −20° C. for 16 h and the suspension filtered. The filtrate was evaporated, the residue was dissolved in Et2O, the solid filtered off and the solvent was evaporated to give crude diamine 301 (1.8 g, 66%) as a yellow oil, which was used without further purification: 1H NMR δ 4.02 (p, J=5.8 Hz, 1H, CHO), 3.58-3.63 (m, 2H, CH2N), 3.25 (s, 3H, OCH3), 2.82-2.87 (m, 2H, CH2N), 2.72 (t, J=6.9 Hz, 2H, NCH2), 2.50 (t, J=7.1 Hz, 2H, NCH2), 1.40-1.60 (m, 4H, NH2, CH2); MS (APCI) m/z 145 (MH+, 100%).

Provenance & Evidence