4-Bromoaniline → HCID 58742411, compound

Participants

Reaction Steps

6.6 g (about 34.4 mmol) of (S)-1-azabicyclo[2.2.2]octane-3-carboxylic acid are heated together with 106 ml of thionyl chloride under reflux for 1 h. The excess thionyl chloride is removed under reduced pressure, and residues are removed by azeotropic distillation together with toluene. The crude acid chloride obtained in this way is stirred together with 5.73 g (33.32 mmol) of 4-bromoaniline and 23.21 ml (133.27 mmol) of N,N-diisopropylethylamine in 30 ml of DMF at RT for 72 h. The solvent is removed under reduced pressure. The crude product is purified by chromatography on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol/triethylamine 70:30:2). The solvent is removed under reduced pressure. Finally, the last residues of solvent are removed under high vacuum. 2.9 g (28% of theory) of the title compound are isolated in a purity of 76%.

Provenance & Evidence