Ammonium → 2-{[2-(2-Dimethylaminoethoxy)-3-pyridinyl]oxy}ethanol

HRID 1765069Notes

Reaction equation

HRID 1765069 reaction equation
N#N.[CH2:3]([O:10][C:11]1[C:12]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:4]1C=CC=CC=1.[NH4+].C(=O)([O-])[O-:25].[K+].[K+].C1(=O)OCCO1>CO.[Pd]>[CH3:22][N:20]([CH3:21])[CH2:19][CH2:18][O:17][C:12]1[C:11]([O:10][CH2:3][CH2:4][OH:25])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

8

Reactant 5

HCID 223AmmoniumHCID 947NitrogenHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 21106669HCID 21106669, compound

Product 1

HCID 117083962-{[2-(2-Dimethylaminoethoxy)-3-pyridinyl]oxy}ethanolYield 46.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a N2-flushed solution of 2-{[3-(benzyloxy)pyridin-2-yl]oxy}-N,N-dimethylethanamine (from Step 2; 8.4 g, 31.1 mmol) in MeOH (100 mL) was added 10% Pd/C (0.8 g) followed by ammonium fornate (6.3 g, 100 mmol). The mixture was stirred at 50° C. under an atmosphere of nitrogen for 2 h. The reaction was filtered through Celite® and the solvent was removed under reduced pressure to yield a semi-crystalline material that was used without further purification in the next synthetic step. The crude product was dissolved in dry DMF (50 mL), potassium carbonate (6.0 g, 43 mmol) was added and the mixture was heated at 150° C. for 20 minutes. Ethylene carbonate (4.1 g, 46 mmol) was added and the heating was continued for another 1.5 h. Solids were filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed on a column of silica using CHCl3/MeOH/NH4OH (95:5:0.2) as eluent to give 3.28 g (31%) of the title product as a light brown oil. HRMS m/z calcd for C11H18N2O3 (M)+ 226.1317. found 226.1323.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. customthe solvent was removed under reduced pressure
  3. customto yield a semi-crystalline material that
  4. customwas used without further purification in the next synthetic step
  5. dissolutionThe crude product was dissolved in dry DMF (50 mL)
  6. temperaturethe mixture was heated at 150° C. for 20 minutes
  7. waitthe heating was continued for another 1.5 h
  8. filtrationSolids were filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was chromatographed on a column of silica

Sources & evidence

ORD record
ord-a1c8b5729121490d9538fd420c60ffbe
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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