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

HRID 1775319Notes

Reaction equation

HRID 1775319 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.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C>[OH:18][NH:17][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

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 14068968tert-Butyl 4-cyanopiperazine-1-carboxylate

Product 1

HCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylateYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-cyanopiperazine-1-carboxylate (1.22 g, 5.77 mmol) in anhydrous ethanol (10 mL) were added hydroxylamine hydrochloride (420 mg, 6.04 mmol) and triethyl amine (843 L, 6.06 mmol). The reaction was heated to reflux for 45 min, after which TLC showed complete consumption of the starting material. The mixture was allowed to cool to room temperature overnight, and the resulting precipitate was removed by filtration. The filtrate was concentrated, yielding 1.42 g of a yellow gel that was used directly in the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 45 min
  3. customconsumption of the starting material
  4. customthe resulting precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c2ded138b444e7cb9954cadb0ff5ad5
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

Loading…