Potassium Carbonate → 2,3-Dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

HRID 565625Notes

Reaction equation

HRID 565625 reaction equation
Br[CH2:2][C:3]1(C)[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.Cl.ClC1C=CC=CC=1N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:2][CH:3]1[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 3

HCID 11430Potassium CarbonateHCID 30170151-(2-Chlorophenyl)piperazinium chlorideHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 178959142,3-Dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g), 1-(2-chlorophenyl)piperazine hydrochloride (1.4 g), and potassium carbonate (2.1 g) in N,N-dimethylformamide (15 mL) was stirred under nitrogen gas at 145° C. for 20 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The pooled organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate (Na2SO4) and silica gel (eluted with ethyl acetate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethylacetate=5:1 to 2:1). The 2-[[4-(2-chlorophenyl)-1-piperazinyl]methyl)]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine thus obtained was dissolved in methanol and a stoichiometric excess of 10% hydrogen chloride solution in methanol was added. The mixture was concentrated under reduced pressure and recrystallized from ethanol/diethyl ether to provide 1.0 g of the title compound. Yield 44%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe pooled organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate (Na2SO4) and silica gel (eluted with ethyl acetate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethylacetate=5:1 to 2:1)

Sources & evidence

ORD record
ord-c015c36be77649e0adf98ba1da03e4e1
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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