4-(2-(Tetrahydropyran-2-yloxy)ethyl)-1-(2-azidoethyl)benzene → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethylamine

HRID 440471Notes

Reaction equation

HRID 440471 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]=[N+]=[N-])=[CH:12][CH:11]=1>C(O)C.[C].[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 224076064-(2-(Tetrahydropyran-2-yloxy)ethyl)-1-(2-azidoethyl)benzene

Product 1

HCID 224076104-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethylamineYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)-1-(2-azidoethyl)benzene (4.30 g, 15.61 mmol) in ethanol was added 10% palladium-carbon (0.10 g). The mixture was stirred under an atmosphere of hydrogen gas at room temperature for 16 hours. Then 10% palladium-carbon was filtered off, and the solvent was evaporated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (=8/2) to give the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethylamine (2.80 g, 72%).

Workup

  1. filtrationThen 10% palladium-carbon was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (=8/2)

Sources & evidence

ORD record
ord-efbfd21867ca40d6bc3ff2f36e1e3992
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

Loading…