Iodocyclopentane → HCID 28814460, compound

HRID 404981Notes

Reaction equation

HRID 404981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[CH:12]1(I)[CH2:16][CH2:15][CH2:14][CH2:13]1>CC#N.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH:8][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 73784IodocyclopentaneHCID 748663-Methoxyphenethylamine

Product 1

HCID 28814460HCID 28814460, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-Methoxyphenethylamine (4.5 mL, 30 mmol), and cyclopentyl iodide (1.15 mL, 10 mmol) in CH3CN (15 mL) were irradiated for 10 min in a microwave at 110° C. After cooling to room temperature the mixture was diluted with CH2Cl2 and washed with NaHCO3 solution. The organic layer was dried over anhydrous Na2SO4 and evaporated in vacuo. The crude product was purified by silica gel chromatography using hexane as eluent and the product N-(3-methoxyphenethyl)cyclopentanamine (1.45 g, 66%) was obtained as a colorless liquid which solidified upon standing. 1H NMR (400 MHz, CDCl3): δ 8.48 (s, 1H), 7.20 (t, 1H, J=8.0 Hz), 6.79-6.73 (overlapping doublets and singlet, 3H), 3.74 (s, 3H), 3.44-3.39 (m, 1H), 3.38-3.11 (m, 4H), 1.84-1.83 (m, 2H), 1.82-1.81 (m, 4H), 1.66-1.56 (m, 2H). LC-MS (ESI) Calcd for: C14H21NO [M+H]+: 220.16. Found: 220.00.

Workup

  1. washwashed with NaHCO3 solution
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated in vacuo
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ed5359e04036438499f2e175b40507e3
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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