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

HRID 2267153Notes

Reaction equation

HRID 2267153 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].[Cl-].[OH:17][NH3+:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[OH:17][NH:18][C:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1)=[NH:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21645Hydroxylamine HClHCID 14068968tert-Butyl 4-cyanopiperazine-1-carboxylate

Product 1

HCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylateYield 86.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a nitrogen atmosphere, a suspension of 7.52 g of tert-butyl 4-cyanopiperazine-1-carboxylate (JMC, 1988, 31, 1036), 7.46 g of hydroxyammonium chloride and 19.7 g of potassium carbonate in 40 ml of ethanol was heated to reflux for 2 hours. The residue prepared by evaporation of the solvent was diluted with ethyl acetate, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 7.51 g of the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe residue prepared by evaporation of the solvent
  4. washwashed with water
  5. dry with materialwith a saturated saline solution and dried over sodium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7907d2e4b2ce4cc387d562b55774d64c
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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