Acetic Anhydride → 4-(1-(N-Acetylamino)cyclopropyl)anisole

HRID 481489Notes

Reaction equation

HRID 481489 reaction equation
[NH2:1][C:2]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(N(CC)CC)C>ClCl.O>[C:13]([NH:1][C:2]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1)(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 125236711-(4-Methoxyphenyl)cyclopropan-1-amine

Product 1

HCID 190664314-(1-(N-Acetylamino)cyclopropyl)anisoleYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24526ChlorineSolvent

Procedure

To a stirred suspension of Compound 7 (1.25 g, 7.66 mmol) in CH2 Cl2 (40 ml) was added acetic anhydride (860 mg, 8.42 mmol) and triethylamine (2.32 g, 22.98 mmol) at room temperature. The reaction mixture was stirred at room temperature for 22 h. The mixture was diluted with H2O (50 ml) and stirred for 10 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with 10% HCl aq., sat. NaHCO3 aq. and brine, dried (MgSO4) and concentrated in vacuo to give crude product (1.58 g, quant.), which was recrystallized from hexane-ethyl acetate to give Compound 8 (1.26 g, 80%) as a white solid.

Workup

  1. stirringstirred for 10 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined solution was washed with 10% HCl aq., sat. NaHCO3 aq. and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude product (1.58 g, quant.), which
  8. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-94aacddcb9e94717af2bf698367018a5
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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