Chloride 2-chloropyridinium 1-oxide → HCID 178453505, compound

HRID 1274977Notes

Reaction equation

HRID 1274977 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:21].C([O-])(O)=O.[Na+]>C(O)(CC)(C)C.CCO>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:21])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 88478Chloride 2-chloropyridinium 1-oxideHCID 516892Sodium BicarbonateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 178453505HCID 178453505, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of N-Boc-1,3-diaminopropane (3.48 g, 20 mmol), 2-chloropyridine N-oxide hydrochloride (3.98 g, 24 mmol), and NaHCO3 (8.40 g, 100 mmol) in tert-amyl alcohol (50 mL) is heated at reflux under argon. After 48 h, the reaction is cooled, diluted with EtOH, filtered, and concentrated. The residue is reconcentrated from toluene and chromatographed (silica gel) to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux under argon
  3. temperaturethe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (silica gel)

Sources & evidence

ORD record
ord-05df74a38b1a43cf85b023cc486ce033
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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