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

HRID 1805790Notes

Reaction equation

HRID 1805790 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-carboxylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (34.38 ml, 443 mmol, 1.1 equiv.) was added slowly to a solution of 1-(tert-butoxycarbonyl)piperazine 6 (BOC-piperazine, 75 g, 403 mmol, 1.0 equiv.) and triethylamine (67.4 ml, 483 mmol, 1.2 equiv.) in methylene chloride (750 ml) while maintaining the internal temperature below 20° C. The solution was stirred at ambient temperature for 24 hours. The solution was poured onto a mixture of ice and water (1.5 L). The phases were separated and the aq. phase was extracted with methylene chloride (800 ml×2). The organic phases were combined, dried over MgSO4, filtered and concentrated to give tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate 7 as an off-white solid (105 g). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 2.75 (s, 3H), 3.15 (m, 4H), 3.50 (m, 4H).

Workup

  1. temperaturewhile maintaining the internal temperature below 20° C
  2. customThe phases were separated
  3. extractionthe aq. phase was extracted with methylene chloride (800 ml×2)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d43e81ecf88c4282b25e7de0659e1c1a
Source dataset
uspto-grants-2013_01
Patent number
US08354528B2

Reaction notes

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