Water → HCID 4634543, compound

HRID 412897Notes

Reaction equation

HRID 412897 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 4634543HCID 4634543, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 1-tert-butoxycarbonylpiperazine (1.86 g, 10.0 mmol) and triethylamine (1.67 mL, 12.0 mmol) in dichloromethane (30 mL) was added 4-fluorobenzenesulfonyl chloride (2.34 g, 12.0 mmol), and the mixture was stirred at room temperature for 24 hours. To the mixture was added water (30 mL). and the mixture was concentrated under reduced pressure. To the concentrate was added ethyl acetate (70 mL). The organic layer was washed with water (30 mL), 1N-hydrochloric acid (10 mL×3), a saturated aqueous solution of sodium hydrogencarbonate (10 mL×3), saturated sodium chloride solution (10 mL), successively, dried over magnesium sulfate and concentrated under reduced pressure. To the concentrate was added diisopropyl ether, and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether, and dried under reduced pressure to give the titled compound (1.94 g, 5.6 mmol, Yield 56%) as white crystals.

Workup

  1. concentrationand the mixture was concentrated under reduced pressure
  2. additionTo the concentrate was added ethyl acetate (70 mL)
  3. washThe organic layer was washed with water (30 mL), 1N-hydrochloric acid (10 mL×3)
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate (10 mL×3), saturated sodium chloride solution (10 mL), successively, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the concentrate was added diisopropyl ether
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. washThe precipitates were washed with diisopropyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-422e293877e54e7c9e5868a5c7faea67
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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