Triethylamine → N-ethoxycarbonyl-m-bromophenethylamine

HRID 257044Notes

Reaction equation

HRID 257044 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][NH2:7].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(Cl)Cl>[CH2:22]([O:21][C:19]([NH:7][CH2:6][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=1)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 70217363-Bromophenethylamine

Product 1

HCID 18963948N-ethoxycarbonyl-m-bromophenethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of m-bromophenethylamine (6.71 g, 33.55 mmol) and Et3N (7 mL, 50.32 mmoL) in CH2Cl2 (100 mL) is cooled to 0° and ethyl chloroformate (4 mL, 50.32 mmoL) is added. After addition is complete the resulting mixture is allowed to come to room temperature and the solvent is removed in vacuo. The residue is then dissolved in EtOAc (200 mL) and the organic phase washed with 2N HCl (1×250 mL), H2O (1×200 mL), saturated NaHCO3 solution (1×200 mL), saturated NaCl solution (1×200 mL), dried over MgSO4 and concentrated in vacuo to give N-ethoxycarbonyl-m-bromophenethylamine.

Workup

  1. additionAfter addition
  2. customto come to room temperature
  3. customthe solvent is removed in vacuo
  4. dissolutionThe residue is then dissolved in EtOAc (200 mL)
  5. washthe organic phase washed with 2N HCl (1×250 mL), H2O (1×200 mL), saturated NaHCO3 solution (1×200 mL), saturated NaCl solution (1×200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee8701aded72479ca304cde5cd352229
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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