2-Chloro-N-(2-chlorophenyl)acetamide → HCID 69746814, compound

HRID 1064571Notes

Reaction equation

HRID 1064571 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:4].[CH3:13][C@H:14]1[CH2:19][NH:18][CH2:17][C@@H:16]([CH3:20])[NH:15]1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:18]1[CH2:17][C@H:16]([CH3:20])[NH:15][C@H:14]([CH3:13])[CH2:19]1

Participants

5

Reactant 3

HCID 2224442-Chloro-N-(2-chlorophenyl)acetamideHCID 516892Sodium BicarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 69746814HCID 69746814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of step (i) (5.9 g) was dissolved in ethanol (50 ml) and cis-2,6-dimethylpiperazine (3 g) and sodium hydrogencarbonate (6.63 g) were added at room temperature under a nitrogen atmosphere. The mixture was heated under reflux for 24 hours and the cooled solution was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in 1M HCl (22 ml) and washed with dichloromethane. The aqueous solution was then basified to pH13 with a solution of sodium hydroxide and the product was extracted with dichloromethane. The organic layer was washed with water, brine, collected, dried (MgSO4) and concentrated under reduced pressure to give the subtitle compound as a beige solid. Yield 4 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. filtrationthe cooled solution was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 1M HCl (22 ml)
  6. washwashed with dichloromethane
  7. extractionthe product was extracted with dichloromethane
  8. washThe organic layer was washed with water, brine
  9. customcollected
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b15c0e84c4e4416b9f2b6d0b7a41641c
Source dataset
uspto-grants-2005_11
Patent number
US06969713B2

Reaction notes

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