1-Methylpiperazine → 4-((4-Methylpiperazin-1-yl)sulfonyl)benzaldehyde

HRID 1697057Notes

Reaction equation

HRID 1697057 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].C([O-])(O)=O.[Na+].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)Cl>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27592104-Formylbenzene-1-sulfonyl chloride

Product 1

HCID 598462224-((4-Methylpiperazin-1-yl)sulfonyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-formylbenzenesulfonyl chloride (1.0 g) in DCM (10 mL) was added NaHCO3 (sat'd aq, 10 mL) followed by 1-methyl-piperazine (0.6 mL). The reaction mixture was vigorously stirred for 1 h, the organic layer separated, and the aqueous layer extracted with DCM (2×20 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give 4-(4-methyl-piperazine-1-sulfonyl)-benzaldehyde (1.28 g) without further purification.

Workup

  1. customthe organic layer separated
  2. extractionthe aqueous layer extracted with DCM (2×20 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5002b60e07d64bbea7b298f33e716d28
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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