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

HRID 1901994Notes

Reaction equation

HRID 1901994 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 hydrochloride that was formed. The filtrate was concentrated to yield a brown gum. The gun 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-[[(phenylsulfonyl)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 hydrochloride that
  5. customwas formed
  6. concentrationThe filtrate was concentrated
  7. customto yield a brown gum
  8. customThe gun 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-9c985cc84e164b179a22604b9ec18847
Source dataset
uspto-grants-1996_11
Patent number
US05578624

Reaction notes

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