Reaction #417943

ord-10572e9e42914c269065c8e47baaf881

Reaction equation

C[C@H](N)c1ccc(Br)cc1
(S)-1-(4-bromophenyl)ethylamine
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)N[C@@H](C)c1ccc(Br)cc1
(S)—N-(1-(4-Bromophenyl)ethyl)acetamide

Reactants

C[C@H](N)c1ccc(Br)cc1
(S)-1-(4-bromophenyl)ethylamine
CC(=O)OC(C)=O
acetic anhydride

Reagents

None

Solvents

ClCCl
DCM

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThen the cooling is removed
  2. 2
    WashAfterwards the mixture is consecutively washed with water, sat. aq. NaHCO3 solution, water, diluted aq. citric acid solution and again water
  3. 3
    Dryinglayer is dried over MgSO4
  4. 4
    Filtrationfiltered
  5. 5
    Otherthe solvent is removed in vacuo

Procedure

To 200 g (1.00 mol) (S)-1-(4-bromophenyl)ethylamine in 800 mL DCM are slowly added 94.5 mL (1.00 mol) acetic anhydride while cooling the mixture to 20-30° C. Then the cooling is removed and the reaction mixture is stirred at r.t. over night. Afterwards the mixture is consecutively washed with water, sat. aq. NaHCO3 solution, water, diluted aq. citric acid solution and again water. The org. layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877741B2uspto-grants-2014_11