Potassium Carbonate → HCID 11659339, compound

HRID 2223787Notes

Reaction equation

HRID 2223787 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[CH3:10][CH:11]([CH3:22])[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][CH:11]([CH3:22])[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21262Aniline, p-(isopentyloxy)-2×HCID 79177tert-Butyl bromoacetate

Product 1

HCID 11659339HCID 11659339, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butylbromoacetate (1.12 g, 0.85 mL, 5.76 mmol) was added drop wise over 5 min to a stirred suspension of {4-[(3-methylbutyl)oxy]phenyl}amine (intermediate 5, 0.85 g, 4.8 mmol) and potassium carbonate (0.66 g, 4.8 mmol) in dimethylformamide (23.4 mL) at room temperature under a nitrogen atmosphere. After stirring for 14 h the volatiles were evaporated and the residue partitioned between dichloromethane (50 mL) and water (50 mL). The phases were separated and the aqueous phase washed with dichloromethane (2×50 mL). The organic phases were combined, dried (magnesium sulfate) then the solvent evaporated. The residue was chromatographed on silica gel (10% diethyl ether:cyclohexane) to give the title compound (inseparable 10:1 mixture of mono- to di-substitution) as a colourless oil (1.38 g). Mono-product: LC/MS: 3.77 min; z/e 294, calcd (M+1) 294. 1H NMR (400 MHz; CDCl3): 0.90 (6H), 1.45 (9H), 1.65 (2H), 1.85 (1H), 3.75 (2H), 3.90 (2H), 6.55 (2H), 6.80 (2H).

Workup

  1. customwere evaporated
  2. customthe residue partitioned between dichloromethane (50 mL) and water (50 mL)
  3. customThe phases were separated
  4. washthe aqueous phase washed with dichloromethane (2×50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on silica gel (10% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-befff2d431fc4120936bc1a735a7e14f
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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