Hydrochloric Acid → 3-(1-Pyrrolidinyl)phenol

Temperature

80 °C

7 g (30 mmol) of 1-Bromo-3-methoxymethoxy-benzene from step A and 2.5 g (35 mmol) of pyrrolidine were dissolved under argon in 60 mL of toluene. Then, 0.15 g (0.3 mmol) of bis(tri-t-butylphosphine)palladium(0), 2.5 g KOH und 0.6 g (0.15 mmol) cetyltrimethylammoniumbromid were added, and the reaction mixture was heated at 80° C. At the end of the reaction, the reaction mixture was poured into 200 mL of ethyl acetate, and the organic phase was extracted with 1N sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using heptane/ethyl acetate (8/0.8). The product thus obtained was dissolved in 15 mL of ethanol and mixed with 10 mL of a 2.9 molar solution of ethanolic hydrochloric acid. The reaction mixture was then heated at 55° C. At the end of the reaction, the precipitate was filtered off, washed with ethanol, and then dried.

1. customAt the end of the reaction
2. extractionthe organic phase was extracted with 1N sodium hydroxide solution
3. dry with materialdried with magnesium sulfate
4. distillationThe solvent was distilled off in a rotary evaporator
5. customthe residue was purified on silica gel
6. customThe product thus obtained
7. temperatureThe reaction mixture was then heated at 55° C
8. customAt the end of the reaction
9. filtrationthe precipitate was filtered off
10. washwashed with ethanol
11. customdried

ORD record

ord-23f99376291041d1bfb0c07596651007

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491244B2