Cyclopentylamine → HCID 17609596, compound

HRID 2272694Notes

Reaction equation

HRID 2272694 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1>O1CCCC1>[CH:1]1([NH:6][C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 17609596HCID 17609596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentanamine (2.7 g, 32 mmol) was added to a solution of 2-chloro-3-nitropyridine (5.0 g, 32 mmol) in tetrahydrofuran (200 mL), and the reaction mixture was stirred at reflux for 18 hours. After removal of solvent under reduced pressure, the residue was purified via silica gel chromatography to give the product as a yellow solid. Yield: 5.5 g, 26 mmol, 81%. 1H NMR (400 MHz, CD3OD) δ 8.42 (dd, half of ABX pattern, J=8.3, 1.8 Hz, 1H), 8.40 (dd, half of ABX pattern, J=4.5, 1.8 Hz, 1H), 6.69 (dd, J=8.3, 4.5 Hz, 1H), 4.51-4.59 (m, 1H), 2.07-2.17 (m, 2H), 1.62-1.85 (m, 4H), 1.51-1.62 (m, 2H)

Workup

  1. temperatureat reflux for 18 hours
  2. customAfter removal of solvent under reduced pressure
  3. customthe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-8fd4f25f2f2648adaf128050b2be72c6
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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