Methanesulfonyl chloride → Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

HRID 844164Notes

Reaction equation

HRID 844164 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].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:15]([CH3:14])(=[O:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

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

Product 1

HCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

N-tert-Butoxycarbonylpiperazine (2.94 g, 16.0 mmol) was dissolved in pyridine (8 mL) under nitrogen and the solution cooled to 0° C. Methanesulfonyl chloride (1.5 mL, 19.3 mmol) was added. After 5 minutes, more pyridine was added (5 mL) and the reaction mixture was allowed to warm to ambient temperature. After 40 minutes, the pyridine was removed in vacuo. The residue was dissolved in ethyl acetate (250 mL), washed with 0.1M citric acid (3×125 mL), dried over magnesium sulfate, concentrated in vacuo, and dried under vacuum to give 3.84 g (92%) of N-tert-butoxycarbonyl-N′-methylsulfonylpiperazine.

Workup

  1. temperatureto warm to ambient temperature
  2. waitAfter 40 minutes
  3. customthe pyridine was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  5. washwashed with 0.1M citric acid (3×125 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2712f9e88a8c48698c0322738f63aa9c
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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