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

HRID 1754055Notes

Reaction equation

HRID 1754055 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. After that the cooling is removed and the reaction mixture is stirred at r.t. over night. Afterwards the mixture is consecutivly washed with water, sat. aq. NaHCO3 solution, water, diluted aq. citric acid solution and water once again. The org. layer is dried over MgSO4 and the solvent is removed in vacuo. The crude product is used without further purification.

Workup

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

Sources & evidence

ORD record
ord-348c04f63ccd43328e4698b2ba9f19c0
Source dataset
uspto-grants-2015_10
Patent number
US09169205B2

Reaction notes

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