Potassium Carbonate → HCID 9801540, compound

HRID 852198Notes

Reaction equation

HRID 852198 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[S:15][CH:16]=2)=[CH:8][CH:7]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:15]1[CH:16]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:25][CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[Cl:21])=[CH:7][CH:8]=2)[C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666482-ChlorobenzylamineHCID 179063143-[4-(3-Bromo-propoxy)-phenyl]-benzo[b]thiophene

Product 1

HCID 9801540HCID 9801540, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 3-[4-(3-bromo-propoxy)-phenyl]-benzo[b]thiophene (0.200 g, 0.576 mmol), 2-chlorobenzylamine (0.326 g, 2.30 mmol), potassium carbonate (0.200 g, 1.45 mmol) and acetonitrile (4.0 ml) and heat (75° C.) overnight. Cool reaction to room temperature, filter through a Waters Sep-Pak 1 g Silica cartridge (ethyl acetate) and concentrate (in vacuo). Purify the crude product by column (silica) chromatography with a graded solvent mixture of 40% ethyl acetate in dichloromethane to 100% ethyl acetate. Concentrate the appropriate fractions, dissolve in dichloromethane and re-evaporate under a stream of nitrogen. Dry sample under vacuum (0.5 mm Hg, 50° C.) overnight to obtain the title compound as a light amber oil (0.184 g, 78% Yield). Purity by LC/MS=98%, [M+H]+=408.

Workup

  1. temperatureCool
  2. customreaction to room temperature
  3. filtrationfilter through a Waters Sep-Pak 1 g Silica cartridge (ethyl acetate)
  4. concentrationconcentrate (in vacuo)
  5. customPurify the crude product by column (silica) chromatography
  6. additionwith a graded solvent mixture of 40% ethyl acetate in dichloromethane to 100% ethyl acetate
  7. concentrationConcentrate the appropriate fractions
  8. dissolutiondissolve in dichloromethane
  9. customre-evaporate under a stream of nitrogen
  10. customDry sample under vacuum (0.5 mm Hg, 50° C.) overnight

Sources & evidence

ORD record
ord-f6d888d3c20d4c2083e766643bba1304
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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