Sodium Iodide → Acetonitrile, [(1,1-dimethylethyl)(phenylmethyl)amino]-

Benzyl(tert-butyl)amine (10.0 g, 61.3 mmol) was dissolved in acetonitrile (100 ml), and bromoacetonitrile (4.5 ml, 64.6 mmol), potassium carbonate (16.9 g, 122.3 mmol) and sodium iodide (9.2 g, 61.4 mmol) were successively added with stirring at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was diluted with saturated aqueous potassium carbonate solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure, and the obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (10.8 g, yield 87%) as a pale-yellow oil.

1. stirringthe mixture was stirred at the same temperature overnight
2. extractionextracted with ethyl acetate
3. washwashed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe insoluble material was filtered off
6. concentrationthe solution was concentrated under reduced pressure
7. customthe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

ORD record

ord-8526684573df4a09b6ad4f40d2002def

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2