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

HRID 2171988Notes

Reaction equation

HRID 2171988 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-71232b33b45241d9aa87c6ec2bec74d4
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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