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

HRID 1853388Notes

Reaction equation

HRID 1853388 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 over MgSO4, filtered 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 over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-ba128c4a263848ddb09448d6fc2cc901
Source dataset
uspto-grants-2015_02
Patent number
US08962641B2

Reaction notes

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