Ethanolamine → HCID 33787778, compound

Temperature

75 °C

A mixture of 3-bromomethyl-pentane (6.0 g, 36.4 mmol) and ethanolamine (13 mL, 218 mmol) in ethanol (45 mL) was heated at 75° C. for 16 h. The reaction mixture was concentrated and the resulting residue was diluted with DCM (70 mL). The organic layer was partitioned with water (70 mL) and the aqueous layer extracted with DCM. Combined organic layers, dried over magnesium sulfate, filtered, and concentrated to give the title compound as an oil (4.90 g). 1H NMR (d6-DMSO, 400 MHz) δ (ppm): 3.44 (t, J=5.6 Hz, 2H), 2.54 (t, J=6.0 Hz, 2H), 2.40 (d, J=5.6 Hz, 2H), 1.31-1.25 (m, 5H), 0.83 (t, J=6.8 Hz, 6H).

1. concentrationThe reaction mixture was concentrated
2. additionthe resulting residue was diluted with DCM (70 mL)
3. customThe organic layer was partitioned with water (70 mL)
4. extractionthe aqueous layer extracted with DCM
5. dry with materialCombined organic layers, dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-5ba82d6be6d24fa68c0ee5a0b681b53b

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481563B2