HCID 57447696, compound → HCID 55285919, compound

Temperature

0 °C

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%).

1. temperatureat reflux temperature for 3 h
2. filtrationthe solid filtered off
3. washwashed with cold EtOH (20 mL) and EtOAc (100 mL)
4. customThe solvent was evaporated to half volume
5. filtrationthe suspension filtered
6. customThe filtrate was evaporated
7. dissolutionthe residue was dissolved in Et2O
8. filtrationthe solid filtered off
9. customthe solvent was evaporated

ORD record

ord-b48900cf1593455bb2e7a73c823db6a7

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2