4-Bromobenzyl bromide → 1-[(4-Bromophenyl)methyl]piperidin-4-amine

To a solution of 4-bromo benzylbromide (1.0 g, 4.1 mmol) in dichloromethane (20 ml) and diisopropyletylamine (1 ml) was added tert-butyl 4-piperidinylcarbamate (1.0 g, 5.0 mmol). The solution was then stirred at room temperature over night. The solvent was evaporated and 25 ml of 50% TFA in dichloromethane was added to the resulting white solid. The mixture was then stirred at room temperature for 2 h and then evaporated to dryness. The resulting solid was dissolved in water and extracted with toluene. After removal of the toluene the water phase was made basic with 1M NaOH giving a pH of 13. The water phase was then extracted with dichloromethane 3 times and the combined extracts were dried and then evaporated to give the pure product as a slightly yellow oil (0.96 g, 3.6 mmol)

1. customThe solvent was evaporated
2. addition25 ml of 50% TFA in dichloromethane was added to the resulting white solid
3. stirringThe mixture was then stirred at room temperature for 2 h
4. customevaporated to dryness
5. dissolutionThe resulting solid was dissolved in water
6. extractionextracted with toluene
7. customAfter removal of the toluene the water phase
8. extractionThe water phase was then extracted with dichloromethane 3 times
9. customthe combined extracts were dried
10. customevaporated

ORD record

ord-05781c454d734c16a82b7b62dcde2f08

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528156B2