Acrylonitrile → 3,3'-[(2-Aminopropane-1,3-diyl)bis(oxy)]dipropanenitrile

Temperature

0 °C

To a suspension of 2-amino-1,3-propandiol (3.0 g, 0.033 mol) in 1,4-dioxane (8 mL) was added aqueous 40% KOH (0.46 mL, 0.003 mol), and the mixture was stirred for 10 minutes. The reaction solution was cooled to 0° C., and acrylonitrile (5.20 mL, 0.079 mol) was added with a syringe. The reaction was then warmed to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was diluted with CH2Cl2 (120 mL) and washed with saturated aqueous NaHCO3 (2×70 mL) and H2O (2×70 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. The resulting residue was purified by flash column chromatography (on silica gel, MeOH:CH2Cl2=1:10 affording 1.62 g (34%) of the desired dinitrile (27) as a slightly yellow liquid. 1H NMR (CDCl3): δ 3.68 (t, J=6.4 Hz, 4H, CH2O), 3.48 (m, 4H, CH2O), 3.15 (m, 1H, CH), 2.61 (t, J=6.4 Hz, 1H, CH2CN).

1. temperatureThe reaction was then warmed to room temperature
2. stirringstirred overnight
3. concentrationconcentrated under reduced pressure
4. additionThe residue was diluted with CH2Cl2 (120 mL)
5. washwashed with saturated aqueous NaHCO3 (2×70 mL) and H2O (2×70 mL)
6. dry with materialThe organic phase was dried over anhydrous MgSO4
7. customthe solvent was removed under reduced pressure
8. customThe resulting residue was purified by flash column chromatography (on silica gel, MeOH

ORD record

ord-36f6c261d8334077a007f05f58161f83

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07862807B2