Potassium Carbonate → N-(2,4-difluorobenzyl)-N-heptyl-2-[4-(2-hydroxyethyl)-2-methoxyphenoxy]acetamide

HRID 898895Notes

Reaction equation

HRID 898895 reaction equation
Br[CH2:2][C:3]([N:5]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:4].[CH2:22]([OH:33])[CH2:23][C:24]1[CH:32]=[CH:31][C:29]([OH:30])=[C:26]([O:27][CH3:28])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[CH2:13][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3](=[O:4])[CH2:2][O:30][C:29]1[CH:31]=[CH:32][C:24]([CH2:23][CH2:22][OH:33])=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16928Homovanillyl alcoholHCID 692602152-Bromo-N-(2,4-difluorobenzyl)-N-heptylacetamide

Product 1

HCID 69258529N-(2,4-difluorobenzyl)-N-heptyl-2-[4-(2-hydroxyethyl)-2-methoxyphenoxy]acetamideYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-N-(2,4-difluorobenzyl)-N-heptylacetamide (135 mg, 0.373 mmol), homovanillyl alcohol (63 mg, 0.373 mmol) and potassium carbonate anhydrous (77 mg, 0.559 mmol) were mixed in acetonitrile (10 ml). The mixture was heated to reflux for 4 hours and then evaporated to dryness. The residue (with additional DCM, 1 ml×2) was loaded onto a column (ISOLUTE® SI, 1 g/6 ml). It was eluted with DCM and then MeOH/DCM (0.5:99.5, then 1:99). The product fractions were combined and evaporated Oil product 132 mg was obtained yield 79%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customevaporated to dryness
  4. washIt was eluted with DCM
  5. customevaporated Oil product 132 mg
  6. customwas obtained yield 79%

Sources & evidence

ORD record
ord-b130aecfd7b4448ea91286d0dd636d55
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

Loading…