Hydroxylamine → tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

HRID 1677737Notes

Reaction equation

HRID 1677737 reaction equation
[C:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[NH2:16][OH:17]>C(O)C>[OH:17][NH:16][C:1](=[NH:2])[N:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 14068968tert-Butyl 4-cyanopiperazine-1-carboxylate

Product 1

HCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylateYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-cyanopiperazine-1-carboxylate (15 g, 76 mmol) in ethanol (150 mL) was added hydroxylamine (50% aqueous solution, 6.2 mL, 92 mmol) and the reaction mixture was stirred at RT for 6 hours. The solvent was evaporated under vacuum and the solid obtained was triturated with hexane (100 mL) and filtered to obtain 15 g (80%) of the title compound as a solid. TLC—Chloroform/methanol (9/1): Rf=0.15.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe solid obtained
  3. customwas triturated with hexane (100 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d3b74edf5e5d4897923b92d89bf254c4
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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