Acetic Anhydride → HCID 19854917, compound

HRID 1649841Notes

Reaction equation

HRID 1649841 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC[O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH:18]2[CH2:20][CH:15]1[CH2:16][CH2:17]2>CCOCC>[C:5]([O:4][CH2:1][CH2:2][O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH:18]2[CH2:20][CH:15]1[CH2:16][CH2:17]2)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19854916Ethanol, 2-[2-(2-azabicyclo[2.2.1]hept-2-yl)ethoxy]-

Product 1

HCID 19854917HCID 19854917, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

198 g (1.94 moles) of acetic anhydride are added to 286 g (1.55 moles) of N-(2-hydroxyethoxyethyl-)2-azabicyclo[2.2.1]heptane (XV) in the absence of moisture such that the temperature is maintained between 50° and 60° C. The mixture is kept boiling for three hours. After cooling 200 ml of ether are added. The product is neutralized with soda solution, is washed until it is neutral, and--after the ether is withdrawn--it is distilled under high vacuum. The main fraction weighs 185 g and contains 99% (XXI). This corresponds to a yield of 52% of theoretical.

Workup

  1. temperatureis maintained between 50° and 60° C
  2. additionare added
  3. washis washed until it
  4. custom--after the ether is withdrawn
  5. distillationit is distilled under high vacuum

Sources & evidence

ORD record
ord-1ab6dc6d0af04e81a6c5dff0d24b577b
Source dataset
uspto-grants-1990_05
Patent number
US04921879

Reaction notes

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