Acetic Anhydride → HCID 58181267, compound

HRID 1465443Notes

Reaction equation

HRID 1465443 reaction equation
Cl.[I:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH:13]3[CH2:15][CH:10]2[CH2:11][NH:12]3)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[C:23]([N:12]1[CH2:11][CH:10]2[CH2:15][CH:13]1[CH2:14][N:9]2[C:6]1[CH:5]=[CH:4][C:3]([I:2])=[CH:8][CH:7]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67266296HCID 67266296, compound

Product 1

HCID 58181267HCID 58181267, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(4-Iodophenyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride (269 mg, 0.80 mmol) was suspended in dichloromethane (0.3 ml), and triethylamine (0.2 ml) and acetic anhydride (0.09 ml, 0.96 mmol) were added. After stirring at room temperature for 1 hr, dichloromethane was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2-acetyl-5-(4-iodophenyl)-2,5-diazabicyclo[2.2.1]heptane (255 mg, yield 93%).

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bc2e74f69f546d8906af00ad2fde989
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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