Acetone → Glycine, N,N-bis(2-cyanoethyl)- (8CI)(9CI)

Temperature

10 °C

Glycine (5 g, 67 mmol) was suspended in water (10 cm3) and TMAH (25% in water, 24.3 g, 67 mmol) was added slowly, keeping the temperature at <30° C. with an ice-bath. The mixture was then cooled to 10° C. and acrylonitrile (7.78 g, 146 mmol) was added. The mixture was stirred overnight, and allowed to warm to room temperature slowly. It was then heated at 50° C. for 2 hours, using a reflux condenser. After cooling with ice, the mixture was neutralized with HCl (6M, 11.1 cm3) and concentrated to viscous oil. This was dissolved in acetone (100 cm3) and filtered to remove NMe4Cl. The filtrate was concentrated under reduced pressure to give an oil that was treated once more with acetone (100 cm3) and filtered to remove more NMe4Cl. Concentration of the filtrate gave 2-(bis(2-cyanoethyl)amino)acetic acid (11.99 g, 99.3%) as a colourless, viscous oil that crystallised over 1 week at room temperature to give a solid product, mp 73° C. (lit mp 77.8-78.8° C. Duplicate 13C signals indicate a partly zwitterionic form in CDCl3 solution.

1. customat <30° C.
2. temperatureto warm to room temperature slowly
3. temperatureIt was then heated at 50° C. for 2 hours
4. temperatureAfter cooling with ice
5. concentrationconcentrated to viscous oil
6. dissolutionThis was dissolved in acetone (100 cm3)
7. filtrationfiltered
8. customto remove NMe4Cl
9. concentrationThe filtrate was concentrated under reduced pressure
10. customto give an oil that
11. filtrationfiltered
12. customto remove more NMe4Cl

ORD record

ord-4d9eda99154f4836a7562e7b03be3e46

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802609B2