Cyclopentylamine → HCID 56828199, compound

HRID 1891420Notes

Reaction equation

HRID 1891420 reaction equation
Cl[CH2:2][CH:3]1[O:5][CH2:4]1.[NH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:7]1([N:6]2[CH2:4][CH:3]([OH:5])[CH2:2]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 7835EpichlorohydrinHCID 516892Sodium Bicarbonate

Product 1

HCID 56828199HCID 56828199, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloro-2,3-epoxypropane (784 μL, 10 mmol) and amino cyclopentane (988 μL, 10 mmol) in dry acetonitrile (10 ml), sodium bicarbonate (1.68 g, 20 mmol) was added, and the resulting mixture was heated to reflux until the completion of reaction (TLC, 5h). The reaction mixture was cooled to room temperature and filtered through Celite. Filtrate was concentrated in vacuo to afford an oily residue, which was purified by flash chromatography (silica gel, EtOAC/MeOH, 9:1) to furnish the title compound (565 mg, 40%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 4.40-4.32 (m, 1H), 3.58-3-53 (m, 2H), 2.90-2.84 (m, 2H), 2.72-2.65 (m, 1H), 1.70-1.23 (m, 8H), ESIMS m/z [M+H]+ 142.5.

Workup

  1. temperaturethe resulting mixture was heated
  2. filtrationfiltered through Celite
  3. concentrationFiltrate was concentrated in vacuo
  4. customto afford an oily residue, which
  5. customwas purified by flash chromatography (silica gel, EtOAC/MeOH, 9:1)

Sources & evidence

ORD record
ord-81fac94db9884e4ebd79d1855198c144
Source dataset
uspto-grants-2013_08
Patent number
US08507539B2

Reaction notes

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