Hydroxyacetonitrile → [(3-Methoxypropyl)(methyl)amino]acetonitrile

A solution of amine hydrochloride 272 (2.6 g, 18.7 mmol), aqueous glycolonitrile (55%, 2.4 mL, 24.7 mmol) and Et3N (4.0 mL, 28.1 mmol) was stirred at 50° C. for 3 h. The solution was cooled and partitioned between water (50 mL) and Et2O (50 mL). The organic fraction was washed with water (2×50 mL) and brine (50 mL), dried and the solvent evaporated to give nitrile 273 (1.94 g, 73%) as a colourless oil; 1H NMR δ 3.53 (s, 2H, CH2CN), 3.42 (t, J=6.3 Hz, 2H, CH2N), 3.33 (s, 3H, OCH3), 2.54 (t, J=7.1 Hz, 2H, CH2), 2.36 (s, 3H, NCH3), 1.73 (tt, J=7.1, 6.3 Hz, 2H, CH2); MS (APCI) m/z 143 (MH+, 100%).

1. temperatureThe solution was cooled
2. custompartitioned between water (50 mL) and Et2O (50 mL)
3. washThe organic fraction was washed with water (2×50 mL) and brine (50 mL)
4. customdried
5. customthe solvent evaporated

ORD record

ord-403a9269e3c344b19f96210805ea8fce

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2