4-Toluenesulfonyl chloride → 1-Acetyl-4-(2-chloroethyl)piperazine

HRID 916451

Reaction equation

HRID 916451 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11]O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.C1(C)C=CC(S([Cl:29])(=O)=O)=CC=1>C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][Cl:29])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 47396291-Acetyl-4-(2-hydroxyethyl)piperazine

Product 1

HCID 132894881-Acetyl-4-(2-chloroethyl)piperazineYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Acetylpiperazin-1-yl)ethanol (500 mg, 2.90 mmol), (prepared as described for the starting material in this example hereinbefore), was dissolved in methylene chloride (10 ml) and triethylamine (445 μl, 3.19 mmol) and 4-toluenesulphonyl chloride (609 mg, 3.19 mmol) were added and the mixture was stirred at ambient temperature overnight. The mixture was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 1-acetyl-4-(2-chloroethyl)piperazine (300 mg, 54%) as an oil.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-2f4d03f2efd1421885b5b5b054254a73
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Linked notes

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