2-Naphthalenesulfonyl chloride → 1-Formyl-4-(2-naphthalenesulfonyl)piperazine

HRID 278544Notes

Reaction equation

HRID 278544 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[CH:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C>C1COCC1>[CH:15]([N:17]1[CH2:22][CH2:21][N:20]([S:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:13])=[O:12])[CH2:19][CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 176421771-Formyl-4-(2-naphthalenesulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF (10 ml) solution of 2-naphthalenesulfonylchloride (23 g, 101 mmol) was added dropwise to a THF (100 ml) solution of 1-formylpiperazine (11.4 g, 100 mmol) and triethylamine (15 g, 150 mmol) under ice-cooling. The solution was stirred at room temperature for 30 minutes, and concentrated. The residue was washed with water and diisopropylether and dried under reduced pressure to give 1-formyl-4-(2-naphthalenesulfonyl)piperazine.

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. washThe residue was washed with water and diisopropylether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2df794ad8eda4be797cd77e112541de3
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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