1-Methylpiperazine → 1-[[(Phenylsulfonyl)hydrazono](2-bromophenyl)methyl]-4-methylpiperazine

HRID 1079904Notes

Reaction equation

HRID 1079904 reaction equation
[C:1]1([S:7]([NH:10][N:11]=[C:12](Cl)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>O1CCCC1>[C:1]1([S:7]([NH:10][N:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])[N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 56975089alpha-Chloro-2-bromobenzaldehyde phenylsulfonylhydrazone

Product 1

HCID 538166591-[[(Phenylsulfonyl)hydrazono](2-bromophenyl)methyl]-4-methylpiperazineYield 124.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution, under nitrogen, of α-chloro-2-bromobenzaldehyde phenylsulfonylhydrazone (271.1 g; 720 mmol) in tetrahydrofuran (THF; 2 L), was added dropwise N-methylpiperazine (159.7 g; 1600 mmol). The reaction was stirred at ambient temperature for three hours, and then permitted to stand at ambient temperature for 16 hours. The reaction was chilled in an ice bath, and then filtered to remove the piperazine hydrochloridethat was formed. The flitrate was concentrated to yield a brown gum. The gum was triturated with hot acetonitrile, the mixture was cooled in an ice bath, and when cold, was filtered to remove unwanted side product. The filtrate was then concentrated to afford 392.9 g of a brown gum of crude 1-[[(phenylsulfon-yl)hydrazono]-(2-bromophenyl)methyl]-4-methylpiperazine.

Workup

  1. waitto stand at ambient temperature for 16 hours
  2. temperatureThe reaction was chilled in an ice bath
  3. filtrationfiltered
  4. customto remove the piperazine hydrochloridethat
  5. customwas formed
  6. concentrationThe flitrate was concentrated
  7. customto yield a brown gum
  8. customThe gum was triturated with hot acetonitrile
  9. temperaturethe mixture was cooled in an ice bath
  10. filtrationwhen cold, was filtered
  11. customto remove unwanted side product
  12. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-f8effeb117c44cb8a90d0681eb01cd5a
Source dataset
uspto-grants-1996_12
Patent number
US05580890

Reaction notes

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