Water → HCID 19369858, compound

HRID 849033Notes

Reaction equation

HRID 849033 reaction equation
Br[CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([OH:16])[C:10]([O:14][CH3:15])=[C:11]([O:12][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(N(CC)CC)C.O>C(OCC)(=O)C>[CH3:15][O:14][C:10]1[C:9]([OH:16])=[C:8]([CH3:17])[C:6]2[CH2:7][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)[O:4][C:5]=2[C:11]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 698734-PhenylpiperidineHCID 19369861HCID 19369861, compound

Product 1

HCID 19369858HCID 19369858, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-bromomethyl-2,3-dihydro-6,7-dimethoxy-2,4-dimethylbenzofuran-5-ol (1.2 g), 4-phenylpiperidine (1.2 g) and triethylamine (1.1 ml) was stirred at under an atmosphere of argon in a sealed tube at 180° C. for 16 hours. After the reaction mixture was cooled, water, triethylamine and ethyl acetate were added, and the mixture was shaken. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to obtain the title compound (0.6 g, 40%).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-01b03fe2373948fb886ebd4027eebd2c
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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