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

HRID 916379Notes

Reaction equation

HRID 916379 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([N:16]1[CH2:15][CH2:14][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:18][CH2:17]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.28 ml) was added dropwise to a solution of 1-(tert-butoxycarbonyl)piperazine (5 g) in methylene chloride (90 ml) containing triethylamine (4.5 ml). The solution was stirred at ambient temperature for 24 hours. The solution was poured onto cooled water and extracted with methylene chloride. The organic phase was separated, washed with brine and dried over magnesium sulphate and evaporated to give tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate (7 g).

Workup

  1. additionThe solution was poured
  2. extractionextracted with methylene chloride
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-84950896a8864a4f9a06cc659daf368c
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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