Bromocyclopentane → 3-(Cyclopentyloxy)-4-methoxyaniline

Temperature

60 °C

A stirred solution of 5-amino-2-methoxyphenol (10 g) in dry dioxane (150 mL) is treated portionwise with an oil suspension of sodium hydride (60%; 3 g; 75 mmol) and the mixture is then warmed at 60° C. for 30 minutes. It is then treated dropwise with a solution of cyclopentyl bromide (9.2 mL) and potassium iodide (50 mg) in dry dimethylformamide (20 mL) and heated at reflux for 5 hours. The mixture is then concentrated and the residue is treated with ethyl acetate (200 mL) and water (200 mL). The organic layer is then separated, washed with water (100 mL), aqueous sodium hydroxide solution (250 mL; 1N), and with water (100 mL), and dried over magnesium sulfate. The concentration of the reaction mixture gives a dark oil, which is subjected to flash chromatography, eluting with a mixture of n-hexane and ethyl acetate (1:1 v/v), to give 3-cyclopentyloxy-4-methoxyaniline (4.43 g), in the form of an oil.

1. temperatureheated
2. temperatureat reflux for 5 hours
3. concentrationThe mixture is then concentrated
4. additionthe residue is treated with ethyl acetate (200 mL) and water (200 mL)
5. customThe organic layer is then separated
6. washwashed with water (100 mL), aqueous sodium hydroxide solution (250 mL; 1N)
7. dry with materialwith water (100 mL), and dried over magnesium sulfate
8. customThe concentration of the reaction mixture gives a dark oil, which
9. washeluting with a mixture of n-hexane and ethyl acetate (1:1 v/v)

ORD record

ord-aebe3bd3a2a54efda85a65705ae92895

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05698711