Acetic Anhydride → HCID 23133281, compound

HRID 1444608Notes

Reaction equation

HRID 1444608 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][N:4]([CH2:13][CH2:14][CH2:15][NH2:16])[CH:3]3[CH2:2]1.C([O-])(O)=O.[Na+].[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)Cl>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][N:4]([CH2:13][CH2:14][CH2:15][NH:16][C:22](=[O:24])[CH3:23])[CH:3]3[CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 23133276HCID 23133276, compound

Product 1

HCID 23133281HCID 23133281, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2,2a,4,5-Tetrahydro-1H-3-aza-acenaphthylen-3-yl)-propylamine (516 mg, 2.39 mmol) was disolved in a vigorously stirred mixture of CH2Cl2 (2.7 ml) and NaHCO3 (sat. solution, 2.7 ml). After the addition of acetic anhydride (348.9 mg, 3.42 mmol), stirring was applied for 90 min at room temperature. Then, the layers were separated. Water (6 ml) was added to the bicarbonate layer and was extracted with CH2Cl2 (3×6 ml). The combined organic layers were dried with Na2SO4, filtered and evaporated too dryness to afford as slightly brown solid identified as the acetylated compound (535 mg, 87% yield).

Workup

  1. customThen, the layers were separated
  2. additionWater (6 ml) was added to the bicarbonate layer
  3. extractionwas extracted with CH2Cl2 (3×6 ml)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated too dryness
  7. customto afford as slightly brown solid

Sources & evidence

ORD record
ord-1ebf97adf4634cbe9cf3d541afca32b1
Source dataset
uspto-grants-2010_02
Patent number
US07662862B2

Reaction notes

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