Triethylamine → Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

HRID 352760Notes

Reaction equation

HRID 352760 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (40 ml), N-tert-butoxycarbonylpiperazine (2.00 g) was dissolved, followed by the addition of triethylamine (1.78 ml). To the resulting solution, methanesulfonyl chloride (0.91 ml) was added dropwise under ice cooling. After stirring for one hour under ice cooling, the reaction mixture was diluted with dichloromethane (20 ml), washed with a 5% aqueous citric acid solution, water and saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was recrystallized from a mixed solvent of ethyl acetate and hexane, whereby the title compound (2.58 g, 91%) was obtained.

Workup

  1. washwashed with a 5% aqueous citric acid solution, water and saturated aqueous NaCl solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas recrystallized from a mixed solvent of ethyl acetate and hexane, whereby the title compound (2.58 g, 91%)
  6. customwas obtained

Sources & evidence

ORD record
ord-177bc834b0634f54b7421a6aa0b6f0cb
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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