Water → Methyl[2-(2-bromophenyl)ethyl]pentylcarbamate

HRID 387637Notes

Reaction equation

HRID 387637 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(N(CC)CC)C.Cl[C:24]([O:26][CH3:27])=[O:25].O>O1CCCC1>[CH3:27][O:26][C:24](=[O:25])[N:10]([CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68476376HCID 68476376, compound

Product 1

HCID 68473838Methyl[2-(2-bromophenyl)ethyl]pentylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.51 g of N-[2-(2-bromophenyl)ethyl]pentan-1-amine in suspension in 120 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 5° C. 2.33 cm3 of triethylamine, then 1.3 cm3 of methyl chloroformate are added to the reaction mixture. This mixture is then stirred for 20 h at a temperature close to 20° C. before being poured over a mixture of water and ice. The phases are stirred for 5 min, then separated. The aqueous phase is extracted 3 times with 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 6.33 g of oil obtained are purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 20% heptane/80% ethyl acetate). After concentrating the fractions under reduced pressure, 5.45 g of methyl[2-(2-bromophenyl)ethyl]pentylcarbamate are obtained in the form of a colorless oil

Workup

  1. customclose to 20° C.
  2. stirringThe phases are stirred for 5 min
  3. customseparated
  4. extractionThe aqueous phase is extracted 3 times with ethyl acetate
  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-43ba9b5d8e6c423588ca8a0454f43ef8
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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