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

HRID 419591Notes

Reaction equation

HRID 419591 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>C(Cl)Cl>[CH3:14][S:15]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

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

Product 1

HCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 1,1-dimethylethyl 1-piperazinecarboxylate (568 g, 3.05 mol) in DCM (4 L) was added TEA (617 g, 6.10 mol). After stirring for 10 min at 0° C., methanesulfonyl chloride (384 g, 3.35 mol) was added via addition funnel. The mixture was stirred at rt overnight. The mixture was poured into H2O (1 L) and extracted with DCM (1 L). The organic layer was separated, washed with H2O (1 L), dried (Na2SO4), and rotovapped down to provide the title compound of step A (720 g, 2.72 mol, 90%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 2.76 (s, 3H), 3.11-3.17 (m, 4H), 3.50-3.53 (m, 4H).

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. extractionextracted with DCM (1 L)
  3. customThe organic layer was separated
  4. washwashed with H2O (1 L)
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-1bc5c8d3b6d14a3cb5e700b6f39c8e0d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…