Iodoethane → 3-[1-Ethyl-2-pyrrolidinyl]phenol

Temperature

100 °C

To a solution of 2-(3-methoxyphenyl)pyrrolidine (3.5 g) in dry acetonitrile (60 ml) was added milled potassium carbonate (4.1 g), followed by iodoethane (1.3 ml) at ambient temperature, under nitrogen, with stirring for 7 hrs. The reaction mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated and the residue was diluted with 48% hydrobromic acid (30 ml) and warmed at 100° C. for 3.5 hrs. Upon cooling to ambient temperature, the reaction mixture was neutralized with saturated sodium bicarbonate solution and the filtrate was extracted with dichloromethane (2 times). The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane/0-10% methanol). The appropriate fractions were collected and concentrated to give 0.8 g (26%) of 3-[1-ethyl-2-pyrrolidinyl]phenol.

1. filtrationThe reaction mixture was filtered through a pad of celite
2. washthe filter cake was washed with ethyl acetate
3. concentrationThe combined filtrates were concentrated
4. additionthe residue was diluted with 48% hydrobromic acid (30 ml)
5. temperatureUpon cooling to ambient temperature
6. extractionthe filtrate was extracted with dichloromethane (2 times)
7. dry with materialThe combined organics were dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by flash column chromatography (silica gel, dichloromethane/0-10% methanol)
11. customThe appropriate fractions were collected
12. concentrationconcentrated

ORD record

ord-16e59a0ff9084c18a80d4092a426c0b3

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591856