Diisopropylethylamine → 1-(Isopropylsulfonyl)piperazine

HRID 31508

Reaction equation

HRID 31508 reaction equation
C([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C.[CH3:23][CH:24]([S:26](Cl)(=[O:28])=[O:27])[CH3:25]>C(Cl)Cl>[CH3:23][CH:24]([S:26]([N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)(=[O:28])=[O:27])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 225628511-(Isopropylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-BOC-piperazine (0.617 mmol) and diisopropylethylamine (0.679 mmol) in 0.5 mL of methylene chloride was added to a 4 mL vial. Propane-2-sulfonyl chloride (0.679 mmol) was added to the vial, and the reaction mixture was shaken overnight at room temperature. When the reaction was complete, it was diluted with 1.5 mL of methylene chloride and extracted with 1 mL of 1N solution of hydrogen chloride followed by 1 mL of 10% potassium carbonate solution. The organic layer was concentrated in vacuo. The residue was dissolved in 0.5 mL of tetrahydrofuran and 4M solution of hydrogen chloride in dioxane (0.5 mL). The solution was shaken overnight at room temperature then concentrated in vacuo to give 1-(propane-2-sulfonyl)-piperazine.

Workup

  1. extractionextracted with 1 mL of 1N solution of hydrogen chloride
  2. concentrationThe organic layer was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 0.5 mL of tetrahydrofuran
  4. stirringThe solution was shaken overnight at room temperature
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-828805a881f8485fbe7897d171c90c4a
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Linked notes

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