Bromine → 4-(2-Aminopropyl)-2-bromo-N,N-dimethylaniline--hydrogen chloride (1/2)

HRID 1973280Notes

Reaction equation

HRID 1973280 reaction equation
[ClH:1].Cl.[CH3:3][N:4]([CH3:15])[C:5]1[CH:14]=[CH:13][C:8]([CH2:9][CH:10]([NH2:12])[CH3:11])=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+].[Br:21]Br>C(O)(=O)C>[ClH:1].[ClH:1].[Br:21][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:5]=1[N:4]([CH3:3])[CH3:15])[CH2:9][CH:10]([NH2:12])[CH3:11]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 30436114-(2-Aminopropyl)-N,N-dimethylaniline--hydrogen chloride (1/2)

Product 1

HCID 30436134-(2-Aminopropyl)-2-bromo-N,N-dimethylaniline--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 2.51 g of 4-dimethylamino-α-methylphenethylamine dihydrochloride and 5.0 g of anhydrous sodium acetate in 50 ml of acetic acid is added dropwise with stirring a solution of 0.51 ml of bromine in 50 ml of acetic acid. The mixture is stirred at room temperature for 2 hours. The solvent is evaporated and the residue dissolved in 200 ml of water. The solution is alkalized with sodium hydroxide and extracted with ether. The ether extract is dried over anhydrous sodium sulphate and acidified with hydrogen chloride in ether. The precipitate is filtered off and recrystallized from ethanol-ethyl acetate. Yield: 2.3 g, m.p. 190°-191°.

Workup

  1. additionis added dropwise
  2. customThe solvent is evaporated
  3. dissolutionthe residue dissolved in 200 ml of water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over anhydrous sodium sulphate
  7. filtrationThe precipitate is filtered off
  8. customrecrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-f8e800c875d341b9982e05b5cfccc191
Source dataset
uspto-grants-1976_12
Patent number
US03996381

Reaction notes

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