Hydrochloric Acid → (p-bromobenzyl)diethyl amine

HRID 924538Notes

Reaction equation

HRID 924538 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.Cl>O.C1COCC1>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromide

Product 1

HCID 10999178(p-bromobenzyl)diethyl amineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with 100 ml diethyl ether for three times
  3. dry with materialThe diethyl ether solution was dried with anhydrous magnesium sulfate over night
  4. customthe magnesium sulfate was removed by filtration
  5. customDiethyl ether was evaporated
  6. customthe raw product was purified by a silica gel column

Sources & evidence

ORD record
ord-d46dacb11eb64f0aa6254e1132213a7f
Source dataset
uspto-grants-2016_03
Patent number
US09279806B2

Reaction notes

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