Acetyl chloride → HCID 19823610, compound

HRID 1650935Notes

Reaction equation

HRID 1650935 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([CH:24]([N:31]([CH3:33])[CH3:32])[C:25](=[O:30])[CH2:26][CH2:27][CH2:28][OH:29])[CH2:23][CH2:22][CH2:21]2)[CH:16]=[CH:17][C:18]=1[Cl:19]>CCOCC>[C:8]([O:29][CH2:28][CH2:27][CH2:26][C:25](=[O:30])[CH:24]([C:20]1([C:15]2[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=2)[CH2:23][CH2:22][CH2:21]1)[N:31]([CH3:33])[CH3:32])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19823848HCID 19823848, compound

Product 1

HCID 19823610HCID 19823610, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Triethylamine and then a solution of acetyl chloride in ether were added dropwise to a solution of the product of Example 45 in ether and the mixture was heated under reflux for 90 minutes, cooled and filtered. The filtrate was diluted with water and extracted with ether. The extract was washed, dried and evaporated to give an oil which was distilled on a Buchi Kugelrohr apparatus (200°/0.5 mm) to give 5-[1-(3,4-dichlorophenyl)cyclobutyl]-5-dimethylamino-4-oxopentyl acetate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. temperaturecooled
  4. filtrationfiltered
  5. additionThe filtrate was diluted with water
  6. extractionextracted with ether
  7. washThe extract was washed
  8. customdried
  9. customevaporated
  10. customto give an oil which
  11. distillationwas distilled on a Buchi Kugelrohr apparatus (200°/0.5 mm)

Sources & evidence

ORD record
ord-484e4e3e9c934c12a69c7f6ab1fd9dd5
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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