Sodium Hydroxide → HCID 21701683, compound

HRID 1596221Notes

Reaction equation

HRID 1596221 reaction equation
Br.[N:2]1([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>O1CCOCC1>[CH:20]1([C:23]([N:5]2[CH2:4][CH2:3][N:2]([NH:8][C:9](=[O:17])[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:7][CH2:6]2)=[O:24])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 21701628HCID 21701628, compound

Product 1

HCID 21701683HCID 21701683, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-piperazinyl-p-fluorobenzamide hydrobromide (500 mg) in 1N aqueous solution of sodium hydroxide (5 ml) and dioxane (5 ml) was added cyclopropanecarbonyl chloride (0.3 ml) at ambient temperature, and the solution was stirred at (he same temperature for 2 hours. After removal of the solvent in vacuo, the residue was dissolved into ethyl acetate and washed with brine (×2). The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was recrystallized from 20% ethanol-water to give N-(4-cyclopropanecarbonyl-1-piperazinyl)-p-fluorobenzamide (0.20 g).

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionthe residue was dissolved into ethyl acetate
  3. washwashed with brine (×2)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from 20% ethanol-water

Sources & evidence

ORD record
ord-94f5c79b3de442db9cb8a35918589e99
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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