Ethanol → 2-(Benzylamino)-1-(3-methoxyphenyl)ethan-1-ol

Temperature

0 °C

In a 250 mL round-bottomed flask, 2-bromo-1-(3-methoxyphenyl)ethanone (3 g, 13.1 mmol) was combined in CHCl3 (55.0 ml) and ethanol (11.0 ml) to give a colorless solution. The solution was cooled to 0° C. Benzylamine (5.61 g, 5.72 ml, 52.4 mmol) was added. After stirring for 0.5 h at 0° C. and then 2 h at room temperature, LCMS indicated that the reaction was mostly complete. (M+H)+=256 m/e. The reaction was cooled again to 0° C. and NaBH4 (743 mg, 19.6 mmol) was added. The reaction was allowed to warm to room temperature and was stirred at this temperature for 2.5 h until reaction was complete. The reaction mixture was quenched with 1M HCl (25 mL) at 0° C. followed by stirring at room temperature for 1 h. The reaction mixture was poured into 150 mL 1 M NaOH and extracted with ethyl acetate (3×150 mL). Combined organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 80 g, 100% ethyl acetate) to yield 2-Benzylamino-1-(3-methoxy-phenyl)-ethanol (1.95 g, 58%). (M+H)|=258 m/e.

1. custom2 h
2. customat room temperature
3. temperatureThe reaction was cooled again to 0° C.
4. temperatureto warm to room temperature
5. stirringwas stirred at this temperature for 2.5 h until reaction
6. customThe reaction mixture was quenched with 1M HCl (25 mL) at 0° C.
7. stirringby stirring at room temperature for 1 h
8. additionThe reaction mixture was poured into 150 mL 1 M NaOH
9. extractionextracted with ethyl acetate (3×150 mL)
10. washCombined organic phase was washed with brine
11. dry with materialdried over MgSO4
12. concentrationconcentrated in vacuo
13. customThe crude material was purified by flash chromatography (silica gel, 80 g, 100% ethyl acetate)

ORD record

ord-3e183a7acd51439e9ff68fdefed3a71f

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353096B2