Cyclobutylamine → HCID 118021805, compound

HRID 518552Notes

Reaction equation

HRID 518552 reaction equation
C1(N)CCC1.[Cl-:6].[N+](C1C=[C:14]([N+]([O-])=O)[CH:13]=[CH:12][C:11]=1[N+:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)([O-])=O>C(O)CCC>[Cl-:6].[CH:11]1([N+:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)[CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 108514191-(2,4-Dinitrophenyl)-3-methylpyridin-1-ium chloride

Product 1

HCID 118021805HCID 118021805, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Cyclobutylamine (2.3 g, 32 mmol) was added to 1-(2,4-dinitrophenyl)-3-methylpyridinium chloride (J. Org. Chem. 1997, 62, 729-33) (8.0 g, 31 mmol) in n-butanol (120 mL) at 20° C. and the deep red solution was refluxed overnight. Concentration under vacuum left a residue that was treated with water (20 mL) and the precipitate was removed by filtration, and the operation was repeated twice. The combined aqueous phase was basified with concentrated ammonia (2 mL) and washed twice with EtOAc. Evaporation of the water to gave the title compound (3.2 g, 70%) as a brown oil. LCMS: 148 M+

Workup

  1. temperaturethe deep red solution was refluxed overnight
  2. concentrationConcentration under vacuum
  3. waitleft a residue that
  4. additionwas treated with water (20 mL)
  5. customthe precipitate was removed by filtration
  6. washwashed twice with EtOAc
  7. customEvaporation of the water

Sources & evidence

ORD record
ord-ef27e1d896e442fdabf51a0d8722100f
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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