Acetic Anhydride → HCID 10469881, compound

HRID 48211Notes

Reaction equation

HRID 48211 reaction equation
[CH2:1]([N:3]1[CH2:12][CH2:11][CH:10]2[C:5](=[C:6]([NH2:14])[CH:7]=[CH:8][CH:9]2[Br:13])[CH2:4]1)[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[Br:13][C:9]1[CH:8]=[CH:7][C:6]([NH:14][C:15](=[O:17])[CH3:16])=[C:5]2[C:10]=1[CH2:11][CH2:12][N:3]([CH2:1][CH3:2])[CH2:4]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 69894940N-ethyl-5-bromo-8-aminotetrahydroisoquinoline

Product 1

HCID 10469881HCID 10469881, compoundYield 67%

Procedure

The product from Example 27 (0.35 mmol) was cooled in an ice bath, treated with acetic anhydride (10 mL), and stirred at room temperature under nitrogen overnight. Excess acetic anhydride was evaporated, the residue washed with ether, and evaporated. The white solid was triturated with ether and collected by filtration. The solid was washed with a mixture of ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with sodium bicarbonate and sodium chloride solutions, dried over MgSO4, filtered, and evaporated. The acetamide was obtained as a white solid (crystallized from ethyl acetate, 0.07 g, 67% yield).

Workup

  1. customExcess acetic anhydride was evaporated
  2. washthe residue washed with ether
  3. customevaporated
  4. customThe white solid was triturated with ether
  5. filtrationcollected by filtration
  6. washThe solid was washed with a mixture of ethyl acetate and saturated sodium bicarbonate
  7. washThe organic layer was washed with sodium bicarbonate and sodium chloride solutions
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-0f2a0dc387fe4e8cbd58f2683dd81b45
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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