Acetic Anhydride → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

HRID 1027911Notes

Reaction equation

HRID 1027911 reaction equation
[C:1]1([NH2:12])[CH:2]=[CH:3][CH:4]=[C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=12.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)C>[C:1]1([NH:12][C:13](=[O:15])[CH3:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21701862HCID 21701862, compound

Product 1

HCID 102623081-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of the product from Example 132A (1.6 g, 9.92 mmol) in ethanol (30 ml) was added a solution of acetic anhydride (1.872 ml, 19.85 mmol) in EtOH (30 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was taken up in EtOAc (100 mL) and the organic solution was washed with H2O, dried and concentrated. The residue was purified by chromatography on silica gel eluting with 15% EtOAc/hexanes to provide the title product. 1H NMR (CDCl3) δ 1.54-1.71 (m, 6H), 1.77-1.89 (m, 2H), 2.20 (s, 3H), 2.72-2.76 (m, J=5.55 Hz, 1H), 2.78-2.85 (m, J=10.71 Hz, 2H), 6.97-7.11 (m, 2H), 7.22 (d, 1H). MS (M+H)+ m/z 204.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washthe organic solution was washed with H2O
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel eluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-d3ba55d3fe964221b3ae2ff9834537a7
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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