O-Methyltyramine → N-[2-(4-methoxyphenyl)ethyl]cyclopentanamine

HRID 404976Notes

Reaction equation

HRID 404976 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[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:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4657O-MethyltyramineHCID 73784Iodocyclopentane

Product 1

HCID 28445893N-[2-(4-methoxyphenyl)ethyl]cyclopentanamineYield 194.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxyphenethyl amine (0.8 mL, 6 mmol), and cyclopentyl iodide (0.22 mL, 2 mmol) in CH3CN (5 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-(4-methoxyphenethyl)cyclopentanamine (0.854 g, 65%) was obtained as a colorless liquid which solidified upon standing. 1H NMR (400 MHz, CDCl3): δ 8.49 (s, 1H), 7.10 (d, 2H, J=8.6 Hz), 6.78 (d, 2H, J=8.6 Hz), 3.74 (s, 3H), 3.69-3.65 (m, 1H), 3.08-3.07 (m, 4H), 1.84-1.83 (m, 2H), 1.82-1.81 (m, 2H), 1.66-1.56 (m, 4H). 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-4cc6a1e5da5645198fa1631f24f53442
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

Loading…