Benzylamine → N-[2-(Cyclopentyl)ethyl]benzenemethanamine

HRID 1164941Notes

Reaction equation

HRID 1164941 reaction equation
[C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(#N)C>[CH:12]1([CH2:11][CH2:10][NH:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 12711948(2-Bromoethyl)cyclopentane

Product 1

HCID 19863445N-[2-(Cyclopentyl)ethyl]benzenemethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 10.7 g (0.1 mol) of benzenemethanamine and 17.7 g (0.1 mol) of (2-bromoethyl)cyclopentane in 100 mL of acetonitrile. Heat the mixture to reflux and follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction remove the solvent in vacuo and add 100 mL of saturated sodium bicarbonate solution. Extract the aqueous mixture with three 100 mL portions of diethyl ether. Dry the combined extracts over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. customthe progress of the reaction by thin-layer chromatography on silica gel
  4. customAt the completion of the reaction remove the solvent in vacuo
  5. additionadd 100 mL of saturated sodium bicarbonate solution
  6. extractionExtract the aqueous mixture with three 100 mL portions of diethyl ether
  7. dry with materialDry the combined extracts over anhydrous sodium sulfate
  8. filtrationFilter the drying agent
  9. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-295ee8f833594ea1ae7a276a0e44e933
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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