Dimethylamine → HCID 86052890, compound

Temperature

45 °C

2-hydroxymethyl-acrylonitrile (37 mmol, 3.1 g, prepared as per procedure described by Csuk et al. in Tetrahedron, 1996, 52, 9759-9776) was treated with dimethylamine (25 mL of a 2M solution in THF) and the reaction was heated in a sealed vessel at 45° C. for 14 h. The reaction was cooled to room temperature and all the volatiles were removed by concentration under vacuum. The crude 2-hydroxymethyl-3-dimethylaminopropionitrile thus obtained was dissolved in dry THF (50-60 mL) and this solution was added dropwise to a cold (−78° C.) suspension of LAH (6 g) in THF (300 ML). The reaction was gradually warmed to room temperature and stirred for an additional 12 h at room temperature. The reaction was then cooled in an ice bath and very carefully quenched by the sequential addition of H2O (6 mL), 4M NaOH (6 mL) and H2O (18 mL). The white slurry thus obtained was filtered through celite and the filter bed was washed with additional CH2Cl2. The entire filtrate was then concentrated under vacuum to provide crude amine 23.

1. temperatureThe reaction was cooled to room temperature
2. customall the volatiles were removed by concentration under vacuum

ORD record

ord-4947c66dc5fa4505a778bf1a497167ef

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642265B2