Hydrochloric Acid → 4-Bromo-N,N-dimethylbenzylamine

HRID 1874075Notes

Reaction equation

HRID 1874075 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][NH:11][CH3:12].Cl>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]([CH3:12])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 685274-Bromobenzyl bromide

Product 1

HCID 2357574-Bromo-N,N-dimethylbenzylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 5° C. 4-bromobenzylbromide (100 g, 402 mmol) in 100 mL DMF is added to a mixture of dimethylamine (40% in water, 150 mL, 1.33 mol). After 0.5 h stirring at RT, 6 M aqueous HCl is added and the reaction mixture is extracted with diethyl ether. The combined organic phases are washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue is purified by vacuum distillation (bp 58° C. at 2 mbar). Yield: 77.6 g.

Workup

  1. customAt 5° C
  2. extractionthe reaction mixture is extracted with diethyl ether
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. distillationThe residue is purified by vacuum distillation (bp 58° C. at 2 mbar)

Sources & evidence

ORD record
ord-82648e249deb4c0b95de0914f5676b32
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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