2-Phenylpropylamine → 2-(4-Bromophenyl)propan-1-amine

HRID 1444544Notes

Reaction equation

HRID 1444544 reaction equation
[C:1]1([CH:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11]Br>CCCCCC.Br.C(OCC)(=O)C>[Br:11][C:4]1[CH:5]=[CH:6][C:1]([CH:7]([CH3:10])[CH2:8][NH2:9])=[CH:2][CH:3]=1

Participants

6

Reactant 2

HCID 113982-PhenylpropylamineHCID 24408Bromine

Product 1

HCID 107986602-(4-Bromophenyl)propan-1-amineYield 23%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenyl-propylamine (1 g, 7.4 mmol) was dissolved in n-hexane (30 mL) and HBr/aq (5 drops) together with ZnBr on silica (1.75 mmol/g, 1 g). Br2 (14.8 mmol, 900 μL) was slowly added and the slurry was stirred over night. The slurry was diluted with ethyl acetate (300 mL) and washed with 2M Na2CO3 (300 mL). The organic phase was dried over Na2SO4, filtered and evaporated to dryness. Purification and separation of regioisomers was done on semi prep-HPLC C18-column (H2O:CH3CN, 1% NH4OAc buffer, gradient 10% to 60% CH3CN, 30 min). Yield 23%

Workup

  1. washwashed with 2M Na2CO3 (300 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification and separation of regioisomers
  6. customwas done on semi prep-HPLC C18-column (H2O:CH3CN, 1% NH4OAc buffer, gradient 10% to 60% CH3CN, 30 min)

Sources & evidence

ORD record
ord-750a5d37858143ed90060188477b4d0c
Source dataset
uspto-grants-2010_02
Patent number
US07662845B2

Reaction notes

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