Bromobenzene → 1-Phenylpiperidine

A 50 mL of reactor equipped with magnetic stir bar was charged with 35 mg (0.05 mmol) of {[(t-Bu)2P(OH)]PdCl2}2 (from Experiment 8), 1.57 g (10.0 mmol) of bromobenzene, 1.02 g (12.0 mmol) of piperidine and 1.35 g (14.0 mmol) of NaO(t-Bu) in 20.0 mL of toluene. The resulting mixture was refluxed for 5 h before the reaction was cooled to room temperature and quenched with 50 mL of H2O. The mixture was transferred to a separatory funnel, and diluted with 300 mL of diethyl ether. The layers were separated, and organic layer was washed with H2O (2×30 mL), brine (30 mL), and dried over mgSO4, filtered, and the ether removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel with hexane/ethyl acetate (50:1 volume ratio). The eluate was concentrated by rotary evaporation followed by high vacuum to give 670 mg (42% yield) of 1-phenylpiperidine.

1. customA 50 mL of reactor equipped with magnetic stir bar
2. temperatureThe resulting mixture was refluxed for 5 h before the reaction
3. customquenched with 50 mL of H2O
4. customThe mixture was transferred to a separatory funnel
5. additiondiluted with 300 mL of diethyl ether
6. customThe layers were separated
7. washorganic layer was washed with H2O (2×30 mL), brine (30 mL)
8. customdried over mgSO4
9. filtrationfiltered
10. customthe ether removed from the filtrate by rotary evaporation
11. customThe resulting residue was chromatographed on silicon gel with hexane/ethyl acetate (50:1 volume ratio)
12. concentrationThe eluate was concentrated by rotary evaporation

ORD record

ord-c5fa004cc8044c83aac6061ba773f187

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762330B2