Potassium Carbonate → HCID 18538581, compound

HRID 412899Notes

Reaction equation

HRID 412899 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl[CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)=[O:18])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2347442-chloro-N-(3,4-dichlorophenyl)acetamideHCID 36998414-(4-Fluoro-benzyl)-piperidine

Product 1

HCID 18538581HCID 18538581, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-fluorobenzyl)piperidine (4.25 g, 22.0 mmol) in DMF (50 mL) were added 2-chloro-N-(3,4-dichlorophenyl)acetamide (Reference Example 70-1, 4.77 g, 20.0 mmol) and potassium carbonate (3.04 g, 22.0 mmol), successively, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and to the concentrate was added ethyl acetate (70 mL). The organic layer was washed with water (20 mL, 10 mL×2), saturated sodium chloride solution (10 mL), successively, dried over magnesium sulfate and concentrated under reduced pressure. To the concentrate was added a mixed solvent of diisopropyl ether/diethyl ether (2/1)(30 mL), and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether (15 mL×4), and dried under reduced pressure to give the titled compound (5.90 g) as white crystals. The filtrate was concentrated. To the concentrate was added a mixed solvent of diisopropyl ether/diethyl ether (2/1)(15 mL), and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether (5 mL×4), and dried under reduced pressure to give the titled compound (1.20 g) as white crystals. Yield: 7.10 g, 90%, 7.10 g, 18.0 mmol.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the concentrate was added ethyl acetate (70 mL)
  3. washThe organic layer was washed with water (20 mL, 10 mL×2), saturated sodium chloride solution (10 mL)
  4. dry with materialsuccessively, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the concentrate was added a mixed solvent of diisopropyl ether/diethyl ether (2/1)(30 mL)
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. washThe precipitates were washed with diisopropyl ether (15 mL×4)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-874ad71ab4f344a38f2ff94b0bc724bd
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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