Triethylamine → 1-(cyclopropylsulfonyl)piperazine hydrochloride

HRID 2403442Notes

Reaction equation

HRID 2403442 reaction equation
C([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(N(CC)CC)C.[CH:21]1([S:24]([Cl:27])(=[O:26])=[O:25])[CH2:23][CH2:22]1>C(Cl)Cl>[ClH:27].[CH:21]1([S:24]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)(=[O:26])=[O:25])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2760919Cyclopropanesulfonyl chloride

Product 1

HCID 666176371-(cyclopropylsulfonyl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To N—BOC-piperazine (1.3 g) in dry DCM (10 ml) was added triethylamine (1.2 mL) and cyclopropanesulphonyl chloride (1.04 g) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was then diluted with DCM, washed with water, dried (MgSO4) and reduced in vacuo. The residue was dissolved in methanol (10 mL) and 4M HCL in dioxane was added (20 mL). After stirring overnight the solvent was reduced in vacuo to yield 1-cyclopropanesulfonyl-piperazine hydrochloride.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. dissolutionThe residue was dissolved in methanol (10 mL)
  4. addition4M HCL in dioxane was added (20 mL)
  5. stirringAfter stirring overnight the solvent

Sources & evidence

ORD record
ord-84797ebed2f14372916a16472743863e
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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