Acetic Anhydride → HCID 19823638, compound

HRID 728284Notes

Reaction equation

HRID 728284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:18]([CH3:20])[CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:21](OCC)(=[O:23])[CH3:22].C(OC(=O)C)(=O)C>O>[C:21]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][CH2:11]1)[N:18]([CH3:20])[CH3:19])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 19823687HCID 19823687, compound

Product 1

HCID 19823638HCID 19823638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product of Example 144 (1.55 g), ethyl acetate (100 ml) and acetic anhydride (20 ml) was heated under reflux for 16 hours, cooled and poured into water. The resulting mixture was basified and extracted with ether. The extract was washed, dried and evaporated to give an oil which was purified by flash chromatography on a silica column using a 9:1 mixture of petroleum ether (b.p. 60°-80° C.) and acetone and then acetone as eluant to give 5-[1-(4-chlorophenyl)cyclobutyl]-5-dimethylaminopentyl acetate as an oil the boiling point of which was not determined.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by flash chromatography on a silica column
  10. additiona 9:1 mixture of petroleum ether (b.p. 60°-80° C.) and acetone

Sources & evidence

ORD record
ord-87e93d321f1a4e3a9181b6019b7b7eb8
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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