Potassium Carbonate → HCID 22011775, compound

HRID 1532962Notes

Reaction equation

HRID 1532962 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][CH2:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:23]2C([NH:26][C:27](=[O:28])[C:22]=12)=O.[C:32](=[O:35])([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17])[CH2:19][CH2:20][C:21]12[CH:31]=[CH:30][CH:29]=[CH:23][CH:22]1[C:27]([NH:26][C:32]2=[O:35])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219600212-BromoethylphthalimideHCID 22011791HCID 22011791, compound

Product 1

HCID 22011775HCID 22011775, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-[2-(2-Benzylaminoethoxy)ethoxy]ethanol 32 (4.786 g, 20 mmol) and 2-bromoethylphthalimide (5.59 mL, 22 mmol) were dissolved in absolute acetonitrile (100 mL). Potassium carbonate (6.91 g, 50 mmol) was added, and the suspension was heated at reflux with vigorous stirring under an argon atmosphere for 18 hours. The suspension was allowed to cool to room temperature, diluted with acetonitrile (100 mL) and filtered through a Celite™ pad. The acetonitrile was removed under reduced pressure and the residue was purified by flash chromatography using a 1:1 mixture of 40% acetone in hexanes and chloroform as the eluent. Fractions contained the desired product (Rf=0.35) were combined, solvent removed under reduced pressure, and the residue dried in vacuo to provide the title compound 33 (4.2 g, 51%). CIMS (MH+): 413. 1H-NMR (CDCl3): δ 7.82 (m, 2H, phthalimide), 7.70 (m, 2H, phthalimide), 7.21 (m, 5H, phenyl), 4.39 (s, 2H, CH2-Ph), 3.70-3.21 (m, 12 H, OCH2CH2O), 2.85 (q, 2H, J=6.1 Hz, phthalimido-ethylene), 2.79 (q, 2H, J=6.4 Hz, phthalimido-ethylene). 13C-NMR (CDCl3): δ 168.8, 139.8, 134.3, 132.8, 129.4, 128.7, 128.0, 127.6, 73.1, 71.0, 70.8, 62.3, 59.9, 53.7, 52.4, 48.2, 45.1.

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux
  3. filtrationfiltered through a Celite™ pad
  4. customThe acetonitrile was removed under reduced pressure
  5. customthe residue was purified by flash chromatography
  6. additiona 1:1 mixture of 40% acetone in hexanes and chloroform as the eluent
  7. customsolvent removed under reduced pressure
  8. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-a0e2c4744e944f2e8aa56ca5fd02e32f
Source dataset
uspto-grants-2001_03
Patent number
US06207660B1

Reaction notes

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