Piperazine → 1-Dansylpiperazine

HRID 863659Notes

Reaction equation

HRID 863659 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[S:7](Cl)([C:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:15]([N:16]([CH3:18])[CH3:17])[C:14]=2[CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8]>C1(C)C=CC=CC=1>[S:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:15]([N:16]([CH3:18])[CH3:17])[C:14]=2[CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 11801Dansyl chloride

Product 1

HCID 117386971-DansylpiperazineYield 168.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dansylpiperazine was prepared by refluxing a solution of 7.98 g piperazine (9.27 mmol) and 5.00 g dansyl chloride (18.5 mmol) in 100 mL toluene for 6 h. The product was isolated by washing the solution with 5% NaOH and then water and concentrating in vacuo to yield 5.0 g (84%) dansylpiperazine as yellow-green powder. 1H NMR (200 MHz, CDCl3) 2.7-2.9 (4H, multiplet), 2.9 (6H, singlet), 3.1-3.3 (4H, multiplet), 7.1-7.6 (3H, multiplet), 8.2-8.6 (3H, multiplet).

Workup

  1. customDansylpiperazine was prepared
  2. customThe product was isolated
  3. washby washing the solution with 5% NaOH
  4. concentrationwater and concentrating in vacuo

Sources & evidence

ORD record
ord-81f9181a594b4c7d85cc809852571288
Source dataset
uspto-grants-1998_02
Patent number
US05721365

Reaction notes

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