Water → HCID 21914287, compound

HRID 1245799Notes

Reaction equation

HRID 1245799 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[N:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][CH2:30][CH2:31]Br.O>CC(N(C)C)=O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([CH:30]([O:29][CH3:28])[CH3:31])[CH2:18][CH2:17]2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 21914335HCID 21914335, compound

Product 1

HCID 21914287HCID 21914287, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-(piperidin-4-yloxy)pyridine trifluoroacetate (0.86 g) was stirred with potassium carbonate (0.838 g) in dimethylacetamide (5 ml). Bromoethyl methyl ether (0.342 ml) was is added and the mixture was heated at 80° C. for 20 minutes. After cooling the mixture was poured into water (30 ml) and extracted three times with ether. The combined extracts were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography eluting with 0 to 2% 2M methanolic ammonia in dichloromethane to give the product as a colourless oil (0.71 g).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted three times with ether
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with 0 to 2% 2M methanolic ammonia in dichloromethane

Sources & evidence

ORD record
ord-8a254309f6294eb19c1ea924900b8547
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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