Tetrahydrofuran → HCID 68476376, compound

HRID 387636Notes

Reaction equation

HRID 387636 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]([NH2:20])[CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].O1CCCC1>C(OCC)(=O)C.O>[Br:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][CH2:6][NH:20][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8060PentylamineHCID 11430Potassium CarbonateHCID 15364878HCID 15364878, compound

Product 1

HCID 68476376HCID 68476376, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7 g of 2-(2-bromophenyl)ethyl methanesulfonate, 14.5 cm3 of 1-pentanamine, 17.33 g of potassium carbonate and 200 cm3 of tetrahydrofuran are stirred at a temperature between 65° C. and 70° C. under an inert atmosphere for 72 h. The reaction mixture is brought to 30° C. in order to be poured over a mixture of water, ice and ethyl acetate. The phases are stirred for 5 min, then are 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 6.6 g of oil obtained are purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 95% dichloromethane/5% methanol to 90% dichloromethane/10% methanol gradient). After concentrating the fractions under reduced pressure, 4.56 g of N-[2-(2-bromophenyl)ethyl]pentan-1-amine are obtained in the form of a white oil.

Workup

  1. customis brought to 30° C. in order
  2. customare separated
  3. extractionThe aqueous phase is extracted 3 times with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-bbc8ba1e73e6449aba1497dccc3ad8a6
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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