Water → HCID 22111025, compound

HRID 565677Notes

Reaction equation

HRID 565677 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[NH:17]1[CH2:22][CH:21]=[C:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:19][CH2:18]1.C(=O)(O)[O-].[K+].O>CN(C)C(=O)C>[CH3:16][C:3]1([CH2:2][N:17]2[CH2:18][CH:19]=[C:20]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH2:21][CH2:22]2)[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 22111025HCID 22111025, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (0.85 g), 3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole (1.1 g) and potassium bicarbonate (0.83 g) in N,N-dimethylactamide (6 mL) was refluxed for 7.5 hours under nitrogen atmosphere. To the mixture water was added and the product was extracted twice with ethyl acetate. The combined extract was washed with water followed by saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from acetone/diisopropyl ether to provide 0.99 g of the title compound. Yield 82%.

Workup

  1. temperaturewas refluxed for 7.5 hours under nitrogen atmosphere
  2. extractionthe product was extracted twice with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1)
  9. customrecrystallized from acetone/diisopropyl ether

Sources & evidence

ORD record
ord-093319ee40ed4356aa24f9e79bdcd985
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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