Water → tert-Butyl 4-(2-(methylsulfonyl)ethyl)piperazine-1-carboxylate

HRID 419500Notes

Reaction equation

HRID 419500 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.[CH:14]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH2:15].C([O-])([O-])=O.[Na+].[Na+].O>C(#N)C>[CH3:19][S:16]([CH2:14][CH2:15][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:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 19354Methyl vinyl sulfoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 66649624tert-Butyl 4-(2-(methylsulfonyl)ethyl)piperazine-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,1-dimethylethyl 1-piperazinecarboxylate (72.8 g, 390 mmol) in acetonitrile (1.4 L) was added methyl vinyl sulfone (50 g, 470 mmol) and Na2CO3 (124 g, 1170 mmol) and the mixture was refluxed overnight. Then the mixture was cooled to rt, and poured into H2O and extracted with EtOAc. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure to give the title compound (106 g, 93% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.41-1.57 (m, 9H), 2.39-2.51 (m, 4H), 2.88 (t, J=8.4 Hz, 2H), 3.02 (s, 3H), 3.14 (t, J=8.4 Hz, 2H), 3.35-3.50 (m, 4H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d6e7efa201d04275a7445f1e32de28fd
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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