Acetic Anhydride → Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]-

HRID 2399256Notes

Reaction equation

HRID 2399256 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([NH:12][C@H:10]([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 31721(+-)-p-Methoxyamphetamine

Product 1

HCID 11769683Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 6 ml of pyridine was dissolved 1.5 g of (-)-2-(p-methoxyphenyl)-1-methylethylamine ([α]D23 : -30.1° (c=1.2, methanol)), and after adding thereto 3 ml of acetic anhydride, the mixture was allowed to stand at room temperature for 1 hour. After distilling off the solvent, the residue was extracted with ethyl acetate. The ethyl acetate extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off and the crude crystals formed were recrystallized from a mixture of n-hexane and benzene to provide 1.8 g of (R)(+)-N-acetyl-2-(p-methoxyphenyl)-1-methylethylamine.

Workup

  1. additionafter adding
  2. distillationAfter distilling off the solvent
  3. extractionthe residue was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customthe crude crystals formed
  9. customwere recrystallized from a mixture of n-hexane and benzene

Sources & evidence

ORD record
ord-f64a6074f5e74b2cb8f5fedda26eaceb
Source dataset
uspto-grants-1995_09
Patent number
US05447958

Reaction notes

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