Methanol → N-[2-(benzyloxy)ethyl]-N-ethylamine

HRID 915917Notes

Reaction equation

HRID 915917 reaction equation
CS(O[CH2:6][CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)=O.CO.[CH2:18]([NH2:20])[CH3:19]>C(Cl)Cl>[CH2:9]([O:8][CH2:7][CH2:6][NH:20][CH2:18][CH3:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 108572722-Benzyloxyethyl mesylate

Product 1

HCID 23009168N-[2-(benzyloxy)ethyl]-N-ethylamineYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To 7.0 g (30 mmol) of 2-(benzyloxy)ethyl methanesulfonate, a 75 ml methanol solution of 2M ethylamine was added, and the mixture was heated at 110° C. in a sealed tube for 2 hours. Then, the reaction mixture was returned to room temperature, and then diluted with methylene chloride. The dilution was washed with a saturated aqueous solution of sodium hydride. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain 3.85 g (72%) of the captioned compound.

Workup

  1. customwas returned to room temperature
  2. washThe dilution was washed with a saturated aqueous solution of sodium hydride
  3. dry with materialThe washed system was dried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-f27245a924294c5ba1f41c9e527faf57
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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