Reaction #1178396

Reaction equation

HCl

potassium carbonate

diethyl amine

p-bromobenzyl bromide

→

(p-bromobenzyl)diethyl amine

Yield 74.0%

Solvents

water

water

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ExtractionThe mixture was extracted with 100 ml diethyl ether for three times
3. 3
   DryingThe diethyl ether solution was dried with anhydrous magnesium sulfate over night
4. 4
   Otherthe magnesium sulfate was removed by filtration
5. 5
   OtherDiethyl ether was evaporated
6. 6
   Otherthe raw product was purified by a silica gel column

Procedure

Into a 500 ml round-bottomed flask were added 150 ml THF, 5 ml water, 2.2 g potassium carbonate, 6 ml diethyl amine, and 5 g p-bromobenzyl bromide. The resultant mixture was refluxed for 12 h. The mixture was then cooled to room temperature, into which 6 ml concentrated HCl was added, followed by the addition of 150 ml water. The mixture was extracted with 100 ml diethyl ether for three times. The diethyl ether solution was dried with anhydrous magnesium sulfate over night and then the magnesium sulfate was removed by filtration. Diethyl ether was evaporated and the raw product was purified by a silica gel column using hexane/chloroform mixture (1:1 by volume) as the eluent. (p-bromobenzyl)diethyl amine (BBDA) was obtained in 74% yield (3.6 g).

Source