Ethanolamine → Ethanol, 2-(phenethylamino)-

Temperature

75 °C

A mixture of 2-bromoethyl benzene (2.0 g, 10.8 mmol) and ethanolamine (3.96 g, 64.8 mmol) in ethanol (11 mL) was heated at 75° C. for 16.5 hours at which time LC/MS showed the reaction was complete. The reaction mixture was then concentrated to remove ethanol and the resulting residue was diluted with DCM (100 mL). The organic layer was partitioned with water (100 mL) and the aqueous layer was extracted with DCM (50 mL). The combined organic layers were washed with water (2×5 mL), dried over sodium sulfate, filtered, and concentrated to give the title intermediate as a light yellowish oil (1.5 g). (m/z): [M+H]+ calcd for C10H15NO, 166.13. found, 166.2) 1H NMR (d6-DMSO, 300 MHz) δ (ppm): 7.13-7.29 (m, 5H), 4.4 (br, 1H), 3.42 (t, J=5.7 Hz, 2H), 2.61-2.76 (m, 4H), 2.55-2.59 (t, J=5.7 Hz, 2H), 1.55 (br, 1H).

1. concentrationThe reaction mixture was then concentrated
2. customto remove ethanol
3. additionthe resulting residue was diluted with DCM (100 mL)
4. customThe organic layer was partitioned with water (100 mL)
5. extractionthe aqueous layer was extracted with DCM (50 mL)
6. washThe combined organic layers were washed with water (2×5 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-12b5dc6ffc0e4477ab396162f33c3533

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263618B2