HCID 57447695, compound → (3-aminopropyl)(2-methoxyethyl)methylamine

Temperature

5 °C

A solution of phthalimide 298 (50.0 g, 181 mmol) and N2H4—H2O (17.5 mL, 362 mmol) in EtOH (500 mL) was stirred at reflux temperature for 2 h. The solution was cooled to 5° C. for 2 h, the precipitate filtered, washed with EtOH (5 mL) and the filtrate evaporated to half volume. The solution was cooled at 5° C. for a further 2 h, the precipitate filtered, washed with EtOH (5 mL) and the filtrate evaporated. The residue was dissolved in 1 M HCl (50 mL), washed with Et2O (2×50 mL) and the pH of the aqueous fraction adjusted to 10 with dilute aqueous NH3 solution. The mixture was extracted with CHCl3 (4×50 mL), the combined organic fraction dried and the solvent evaporated to give diamine 299 (Sandberg, R., et al., Acta Pharmaceutica Suecica 1979, 16, 386-395) as a pale yellow oil (25.2 g, 95%) which was used without further purification: 1H NMR [(CD3)2SO] δ 3.38 (t, J=6.0 Hz, 2H, CH2O), 3.21 (s, 3H, OCH3), 2.60 (t, J=6.8 Hz, 2H, CH2N), 2.46 (t, J=6.0 Hz, 2H, CH2N), 2.36 (t, J=7.0 Hz, 2H, CH2N), 2.14 (s, 3H, NCH3), 1.50 (p, J=7.0 Hz, 2H, CH2), NH2 not observed; HRMS (Cl+) calcd for C7H17N2O (M-H+) m/z 145.1341, found 145.1337.

1. temperatureat reflux temperature for 2 h
2. filtrationthe precipitate filtered
3. washwashed with EtOH (5 mL)
4. customthe filtrate evaporated to half volume
5. temperatureThe solution was cooled at 5° C. for a further 2 h
6. filtrationthe precipitate filtered
7. washwashed with EtOH (5 mL)
8. customthe filtrate evaporated
9. dissolutionThe residue was dissolved in 1 M HCl (50 mL)
10. washwashed with Et2O (2×50 mL)
11. extractionThe mixture was extracted with CHCl3 (4×50 mL)
12. customthe combined organic fraction dried
13. customthe solvent evaporated

ORD record

ord-92baf2ce0a18465f871feef56b453e80

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2