Ethanolamine → HCID 21951129, compound

Participants

Reaction Steps

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]+.

Provenance & Evidence