1-Heptanamine → 2-(4-bromo-phenyl)-N-heptyl-acetamide

A stirred solution of (4-bromo-phenyl)-acetic acid (0.186 mol, 40.0 g) and thionyl chloride (0.558 mol, 40.0 mL) in chloroform (500 mL) under a N2 atmosphere was heated under reflux for 20 hours. The mixture was cooled to room temperature and evaporated under vacuum to give an oil. This was dissolved in anhydrous methylene chloride (150 mL) and added dropwise to a solution of heptylamine (0.20 mol, 30.3 mL) and N,N-diisopropylethylamine (0.37 mol, 64.7 mL) in anhydrous methylene chloride cooled to 0° C. The mixture was stirred at room temperature for 45 minutes then poured into water and extracted with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The solid residue was purified by crystallization from ethyl acetate/hexanes to give 2-(4-bromo-phenyl)-N-heptyl-acetamide as a white solid. (37 g, 64%)

1. temperatureunder reflux for 20 hours
2. customevaporated under vacuum
3. customto give an oil
4. temperaturecooled to 0° C
5. extractionextracted with methylene chloride
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was removed under vacuum
9. customThe solid residue was purified by crystallization from ethyl acetate/hexanes

ORD record

ord-25fe1573b1714939984f8e042e7152fd

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06699904B2