Acetic Anhydride → N-((1S)-1-(4-Bromophenyl)ethyl)acetamide

HRID 40558Notes

Reaction equation

HRID 40558 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 793484N-((1S)-1-(4-Bromophenyl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

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 with MgSO4 and the solvent is removed in vacuo. The crude product is used without further purification.

Workup

  1. customThen the cooling is removed
  2. washAfterwards the mixture is consecutively washed with water, sat. aq. NaHCO3 solution, water, diluted aq. citric acid solution and again water
  3. dry with materiallayer is dried with MgSO4
  4. customthe solvent is removed in vacuo
  5. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-79330a88ee4444a18d3c367b1401b50e
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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