Potassium Carbonate → HCID 22111024, compound

HRID 565683Notes

Reaction equation

HRID 565683 reaction equation
I[CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([NH2:16])[C:10]([CH3:15])=[C:11]([CH:12]([CH3:14])[CH3:13])[C:5]=2[O:4]1.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[CH:12]([C:11]1[C:5]2[O:4][C:3]([CH3:18])([CH2:2][N:28]3[CH2:29][CH2:30][CH:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[CH2:7][C:6]=2[C:8]([CH3:17])=[C:9]([NH2:16])[C:10]=1[CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 22111007HCID 22111007, compound

Product 1

HCID 22111024HCID 22111024, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A suspension of 2,3-dihydro-2-(iodomethyl)-7-isopropyl-2,4,6-trimethyl-5-benzofuranamine (1.1 g), 4-phenylpiperidine (0.87 g) and potassium carbonate (0.83 g) in N,N-dimethylacetamide (6 mL) was refluxed for 4.5 hours. The mixture was diluted with water and the product was extracted twice with ethyl acetate. The combined organic layer was washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate, filtrated and evaporated in vacuo. The residue was purified with basic silica gel column chromatography (hexane:ethyl acetate=30:1 to 10:1) and recrystallized from hexane/ethyl acetate to afford 0.55 g of the title compound. Yield 47%.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customevaporated in vacuo
  7. customThe residue was purified with basic silica gel column chromatography (hexane:ethyl acetate=30:1 to 10:1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-32e5da82b4ab42888d92238d1358bece
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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