Triethylamine → tert-butyl 2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

HRID 82932Notes

Reaction equation

HRID 82932 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]#[N:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C>[NH2:15]/[C:14](=[N:17]\[OH:18])/[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 2756784Tert-butyl 2-cyanopiperidine-1-carboxylate

Product 1

HCID 45833400tert-butyl 2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 16 mL vial, N-boc-2-cyanopiperidine (500 mg, 2.38 mmol) was dissolved in ethanol (6.7 mL), then hydroxylamine hydrochloride (231 mg, 3.33 mmol) and triethylamine (0.56 mL, 4.05 mmol) were added. The reaction mixture was stirred at reflux for 5 h, cooled and concentrated. The residue was taken up in EtOAc and water. The two layers were separated and the aqueous phase extracted with EtOAc. The combined organics were dried on Na2SO4 and concentrated to give the product as a white solid (550 mg, 95%).

Workup

  1. temperatureat reflux for 5 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe two layers were separated
  5. extractionthe aqueous phase extracted with EtOAc
  6. customThe combined organics were dried on Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6a2f5787617545baaa175950e7766de4
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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