Potassium Carbonate → 2-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine

HRID 387641Notes

Reaction equation

HRID 387641 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14])(=O)=O.[CH2:15]([O:17][CH2:18][CH2:19][NH2:20])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][CH2:6][NH:20][CH2:19][CH2:18][O:17][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66970EthoxyethylamineHCID 15364878HCID 15364878, compound

Product 1

HCID 684705122-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g of 2-(2-bromophenyl)ethyl methanesulfonate, 5.59 g of 2-ethoxyethanamine, 8.67 g of potassium carbonate and 70 cm3 of tetrahydrofuran are stirred under the reflux of the solvent under an inert atmosphere for 48 h. The heating is stopped, then the reaction mixture is filtered. The insoluble material is washed twice with ethyl acetate. The filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). The product obtained is purified by flash chromatography over silica (column: 330 g; particle size: 20-40 μm, spherical; eluent: 100% ethyl acetate to 90% ethyl acetate/10% methanol gradient). After concentrating the fractions under reduced pressure, 2.45 g of 2-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine are obtained in the form of a yellow oil.

Workup

  1. temperaturereflux of the solvent under an inert atmosphere for 48 h
  2. filtrationthe reaction mixture is filtered
  3. washThe insoluble material is washed twice with ethyl acetate
  4. concentrationThe filtrate is concentrated
  5. customa rotary evaporator under reduced pressure (5 kPa)
  6. customThe product obtained
  7. customis purified by flash chromatography over silica (column: 330 g; particle size: 20-40 μm, spherical; eluent: 100% ethyl acetate to 90% ethyl acetate/10% methanol gradient)
  8. concentrationAfter concentrating the fractions under reduced pressure, 2.45 g of 2-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine
  9. customare obtained in the form of a yellow oil

Sources & evidence

ORD record
ord-ec8a03b675bb4e06be24ae3e8cea9adb
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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