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

HRID 2185510Notes

Reaction equation

HRID 2185510 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl>[C:13]1([CH2:12][CH2:11][NH:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 69451-Chloro-2-nitrobenzene

Product 1

HCID 2920933(2-Nitrophenyl)(2-phenylethyl)amineYield 97.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloro-2-nitrobenzene (2 g, 12.7 mmol), phenethylamine (5.1 mL, 40.6 mmol), and N,N-diispropylethylamine (2.8 mL, 15.3 mmol) were dissolved in 1,2-dichloroethane (20 mL) and heated at reflux for 16 hrs. The mixture was concentrated to an oil which was dissolved in EtOAc (200 mL), washed with dilute HCl (3×50 mL), dried over Na2SO4, filtered and concentrated to dryness to give the title compound (3.0g, 97%): 1H NMR (400 MHz, CDCl3) δ 3.0-3.1 (2H, t), 3.5-3.65 (2H, q), 6.65-6.7 (1H, t), 6.85-6.9 (1H, d), 7.25-7.4 (5H, m), 7.45-7.5 (1H, t), 8.15-8.2 (1H, d).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hrs
  3. concentrationThe mixture was concentrated to an oil which
  4. dissolutionwas dissolved in EtOAc (200 mL)
  5. washwashed with dilute HCl (3×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7842f2f419574a3eab6222a54fee682d
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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