Ammonia → HCID 11731626, compound

HRID 497322Notes

Reaction equation

HRID 497322 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14](Cl)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[NH3:23]>O>[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:23]2[CH2:11][CH2:12][N:7]([CH3:5])[CH2:8][CH2:9]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22318640HCID 22318640, compound

Product 1

HCID 11731626HCID 11731626, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 7.6 g of 1-ethoxycarbonyl-4-[2-chloro-2-(4-fluorophenyl)ethyl]piperazine hydrochloride were poured 5 ml of 25% aqueous ammonia solution and water and, after extraction with ether, the organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in 20 ml of benzene, and 5.4 ml of 1-methylpiperazine was added, followed by heating at 65° C. for 3.5 hours. To the reaction solution were poured 25% aqueous ammonia solution and water and, after extraction with ether, the organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=4:1) to give 6.58 g of 1-ethoxycarbonyl-4-[2-(4-fluorophenyl)-2-(4-methylpiperazino)ethyl]piperazine as an oil.

Workup

  1. extractionafter extraction with ether
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 20 ml of benzene
  7. addition5.4 ml of 1-methylpiperazine was added
  8. additionTo the reaction solution were poured 25% aqueous ammonia solution and water
  9. extractionafter extraction with ether
  10. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  11. customAfter removal of the drying agent
  12. filtrationby filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ba2c8217d48948c0abeecc5f6b6ceb3f
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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