Water → HCID 66818770, compound

HRID 1755015Notes

Reaction equation

HRID 1755015 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.Cl.Cl[CH2:15][CH2:16][NH2:17].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:15][CH2:16][NH2:17]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6764944-BromoindoleHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 66818770HCID 66818770, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

Tetrabutylammonium hydrogen sulfate (41.0 mg, 0.121 mmol) and sodium hydroxide (210 mg, 5.25 mmol) were added to a solution of 4-bromo-1H-indole (0.30 ml, 2.39 mmol) in acetonitrile (0.80 mL), and the mixture was stirred at room temperature for 20 minutes. Subsequently, 2-chloroethylamine hydrochloride (334 mg, 2.88 mmol) was added and the mixture was heated with stirring at 100° C. for seven hours. After cooling, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 2-(4-bromo-indol-1-yl)-ethylamine (222 mg, 39%).

Workup

  1. temperaturethe mixture was heated
  2. stirringwith stirring at 100° C. for seven hours
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with water and saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-fab6e8c5118e45e4a854b2f40e76bcdc
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…