Potassium Iodide → 4-ethyl-N-(2-methylpropyl)aniline

Temperature

150 °C

A mixture of 2-methyl-1-propanol (5.94 mL, 64.40 mmol), 4-ethylaniline (2 mL, 16.09 mmol), potassium iodide (5.342 g, 32.2 mmol) and [Cp*IrCl2]2 (128 mg, 0.161 mmol) was prepared in water (10 mL). This mixture was heated by microwaves to 150° C. for 1.5 hours. After cooling, the reaction mixture was diluted with dichloromethane (20 mL) and water (10 mL) then stirred vigorously for 3 minutes. The organic phase was separated (hydrophobic frit) and the aqueous phase was diluted with further dichloromethane (10 mL) then stirred vigorously for 2 minutes and separated (hydrophobic frit). The combined organic fractions were evaporated in vacuo to give the crude product as a brown oil. The crude was purified by flash silica (Si) chromatography (using a 0-50% dichloromethane-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound as a pale yellow oil. (1.9285 g, 77%). LCMS (M+1) 178, RT 0.91 mins.

1. temperatureAfter cooling
2. customThe organic phase was separated (hydrophobic frit)
3. additionthe aqueous phase was diluted with further dichloromethane (10 mL)
4. stirringthen stirred vigorously for 2 minutes
5. customseparated (hydrophobic frit)
6. customThe combined organic fractions were evaporated in vacuo
7. customto give the crude product as a brown oil
8. customThe crude was purified by flash silica (Si) chromatography (
9. customevaporated in vacuo

ORD record

ord-06c9c1f80dc048d3816027431a7a062e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150508B2