Benzylamine → HCID 10703903, compound

HRID 400475Notes

Reaction equation

HRID 400475 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:10][CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 10703903HCID 10703903, compoundYield 151.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

12 g Benzylamine and 25 g 4-bromo-1-buten were added to a suspension of 46 g potassium carbonate in 150 mL DMF and the mixture was heated at 50° C. for 16 h. The reaction mixture was cooled to RT, diluted with ethyl acetate, washed with water and brine, dried, concentrated, and purified by chromatographie on silica gel (hexane/ethyl acetate 50:1) to yield 18.3 g of the desired product. (M+H)+: 230

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by chromatographie on silica gel (hexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-d8cdbf5fb2f1448ea64f133badeb276a
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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