Cyanogen Bromide → HCID 178508456, Verbindung

To a solution of N-benzylethane-1,2-diamine (1.00 g, 6.65 mmol) in absolute ethanol (25 mL) was added cyanogen bromide (0.92 g, 8.65 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, then cooled in an ice water bath. The pH of the solution was adjusted to ˜10 by the addition of 1 M sodium hydroxide solution dropwise. The solvent was concentrated in vacuo. The residue was diluted with ethyl acetate (100 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the concentrated in vacuo. The residue was recrystallized in ethyl acetate and hexane to yield the title compound as a colorless solid in 96% yield (1.12 g): mp 165-167° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 7.39-7.24 (m, 6H), 4.47 (s, 2H), 3.49-3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 159.4, 136.0, 129.1, 128.2, 128.1, 48.1, 47.4, 41.3; MS (ES+) m/z 176.3 (M+1).

1. temperaturecooled in an ice water bath
2. concentrationThe solvent was concentrated in vacuo
3. additionThe residue was diluted with ethyl acetate (100 mL)
4. washwashed with water (200 mL) and brine (100 mL)
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationthe concentrated in vacuo
8. customThe residue was recrystallized in ethyl acetate

ORD-Eintrag

ord-4e673c1aeb2f403cab3e95cab44409aa

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08063084B2