Piperazine → HCID 14626286, compound

HRID 477795Notes

Reaction equation

HRID 477795 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:3]1=2.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:17][C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:3]=2[CH:16]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 14626285HCID 14626285, compound

Product 1

HCID 14626286HCID 14626286, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 15 g of 11-chloro-2-fluoro-6,11-dihydrodibenz[b,e]oxepin, which is prepared according to the procedure of Reference Example 1, in 300 ml of chloroform is added a solution of 25 g of anhydrous piperazine in 50 ml of chloroform at 0° C. After the temperature of the reaction mixture is raised to room temperature over 2 hours, it is added with 10% aqueous sodium hydroxide and extracted with chloroform. After the extract is washed with a saturated saline solution and dried over anhydrous potassium carbonate, the solvent is distilled off under reduced pressure. After the residue is added with 500 ml of toluene, an excess amount of piperazine is distilled off under reduced pressure to give 12 g of the objective compound as an oil. Mass spectrum m/z:298(M+).

Workup

  1. extractionextracted with chloroform
  2. washAfter the extract is washed with a saturated saline solution
  3. dry with materialdried over anhydrous potassium carbonate
  4. distillationthe solvent is distilled off under reduced pressure
  5. additionAfter the residue is added with 500 ml of toluene
  6. distillationan excess amount of piperazine is distilled off under reduced pressure

Sources & evidence

ORD record
ord-6fb3b99904c54b92b594e243b47100b6
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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