Ethanolamine → HCID 21951129, compound

To a stirring solution of ethanolamine (7.5 mL, 124 mmol), nitropropane (11.1 mL, 124 mmol), water (2.4 mL) in isopropanol (21 mL) was added 5 N NaOH (148 uL, 0.74 mmol) followed by the slow addition of 37% aq formaldehyde (9.2 mL). The resulting mixture was stirred for 19 hours at room temperature, then diluted with 130 mL of 1 N HCl. The mixture was successively washed with ether and ethyl acetate, then the pH was adjusted to about 10 with 50% NaOH. The basic solution was extracted twice with dichloromethane. The combined organic fractions were concentrated under reduced pressure to give 17.4 g of a pale yellow liquid. 1H NMR (CDCl3, 400 MHz) δ 1.60 (s, 6H), 2.79-2.82 (t, J=5.1 Hz, 2H), 3.04 (s, 2H), 3.60-3.62 (t, J=5.1 Hz, 2H). LRMS (ESI/APCI) m/z 163 [M+H]+.

1. washThe mixture was successively washed with ether and ethyl acetate
2. extractionThe basic solution was extracted twice with dichloromethane
3. concentrationThe combined organic fractions were concentrated under reduced pressure

ORD record

ord-93eadef67f2e4c7192a64c108b4de5da

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248117B2