Phenethylamine → (2-Nitrophenyl)(2-phenylethyl)amine

HRID 1461254Notes

Reaction equation

HRID 1461254 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(N(CC)CC)C.[CH2:18]([NH2:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:18]([NH:26][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2920933(2-Nitrophenyl)(2-phenylethyl)amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1-fluoro-2-nitrobenzene (14.1 g, 0.1 mol) and triethylamine (14 ml, 0.1 mol) in DMF (150 ml) was added phenethylamine (12.1 g, 0.1 mol). The mixture was now heated to 100° C., and the reaction was monitored by TLC. After the reaction was completed (2 h) the solvent was removed by evaporation in vacuo. The residue was partitioned between 0.5N aqueous HCl (100 ml) and ether (100 ml). The organic phase was washed with water, dried and evaporated to give the title compound as a yellow oil.

Workup

  1. custom(2 h)
  2. customwas removed by evaporation in vacuo
  3. customThe residue was partitioned between 0.5N aqueous HCl (100 ml) and ether (100 ml)
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1d5a6e1bb5924e7ca89b14d961c75816
Source dataset
uspto-grants-1991_12
Patent number
US05075304

Reaction notes

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