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

HRID 1461825Notes

Reaction equation

HRID 1461825 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 N2, of the α-chloro-2-bromobenzaldehyde phenylsulfonylhydrazone (271.1 g. 0.72 mol) of Example 1b in tetrahydrofuran (THF) [2 l], was added, dropwise, N-methylpiperazine (159.7 g, 11.6 mol). The reaction was stirred at ambient temperature for 3 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. The filtrate was concentrated to yield a gum. The gum was triturated with hot CH3CN, the mixture was cooled in an ice bath and when cold it was filtered. The filtrate was then concentrated to afford 392.9 g of 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
  5. concentrationThe filtrate was concentrated
  6. customto yield a gum
  7. customThe gum was triturated with hot CH3CN
  8. temperaturethe mixture was cooled in an ice bath
  9. filtrationwhen cold it was filtered
  10. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-b542d040e61743f9b1e4981d581469e6
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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