Sulfamide → tert-Butyl 4-sulfamoylpiperazine-1-carboxylate

HRID 1669401Notes

Reaction equation

HRID 1669401 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[N:6]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10]N[CH2:8][CH2:7]1>O1CCOCC1>[NH2:4][S:1]([N:5]1[CH2:10][CH2:11][N:6]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:7][CH2:8]1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 53628347tert-Butyl 4-sulfamoylpiperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfamide (5 eq) was added to a solution of tert-butyl piperazine-1-carboxylate in dioxane (0.12 M). The reaction was stirred at reflux overnight. The solvent was removed in vacuo, the residue taken up in EtOAc and washed with H2O, brine, before being dried (Na2SO4), filtered and concentrated in vacuo to give the crude material. Purification was by automated FC (EtOAc:PE:Et3N 40:60:0.02) to afford the title compound (70%). 1H NMR (300 MHz, DMSO-d6, 300 K) δ 1.39 (s, 9H), 2.88-2.90 (m, 4H), 3.37-3.39 (m, 4H), 6.78 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed in vacuo
  3. washwashed with H2O, brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material
  8. customPurification

Sources & evidence

ORD record
ord-539387de13424ace964af61e5c608f91
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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