Benzylamine → N-benzyl-2-(2-bromophenyl)ethanamine

HRID 387631Notes

Reaction equation

HRID 387631 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.[C:15]1([CH2:21][NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>O.C(OCC)(=O)C>[CH2:21]([NH:22][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 15364878HCID 15364878, compound

Product 1

HCID 11055371N-benzyl-2-(2-bromophenyl)ethanamineYield 235.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.18 g of 2-(2-bromophenyl)ethyl methanesulfonate, 6.2 g of 1-phenylmethanamine, 7.87 g of potassium carbonate and 65 cm3 of tetrahydrofuran are stirred under an inert atmosphere for 16 h under the reflux of the solvent. The reaction mixture is cooled to a temperature close to 20° C., then in ice. 100 cm3 of ethyl acetate and 200 cm3 of water are then added thereto. Stirring is continued for 5 min. The aqueous phase is extracted using ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). The 7.8 g of brown oil obtained are purified by flash chromatography over silica (column: 400 g; particle size: 15-40 μm; eluent: 100% dichloromethane to 90% dichloromethane/10% methanol gradient). After concentrating the fractions under reduced pressure, 2.49 g of N-benzyl-2-(2-bromophenyl)ethanamine are obtained.

Workup

  1. temperaturereflux of the solvent
  2. temperatureThe reaction mixture is cooled to a temperature
  3. customclose to 20° C.
  4. extractionThe aqueous phase is extracted
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-e2a878939cf44c80abbd515326b148cf
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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